Chewing Gum Containing Physiological Cooling Agents

ABSTRACT

A method for producing a chewing gum, as well as the chewing gum so produced, incorporates a physiological cooling agent, such as acyclic carboxamide, or combinations of physiological cooling agents. In another embodiment a combination of physiological cooling agents is made in a modified release structure. The modified release/cooling agents combination is preferably obtained by physically modifying the properties of the combination of cooling agents by coating and drying. When incorporated into gum, these particles are adapted to enhance the shelf stability of the flavor and/or produce a modified release when the gum is chewed. In another embodiment, the physiological cooling agent is present with menthol and menthone. 
     In another embodiment, coated chewing gum has a coating that comprises a physiological cooling agent. The preferred inventive chewing gum provides a high flavor impact in which the harsh notes normally associated with such a high flavor impact have been reduced or eliminated. In addition, the preferred inventive gum provides a clean, high-quality, cooling chewing gum coating with xylitol or other polyols where xylitol has been reduced in concentration or eliminated.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a continuation of U.S. patent applicationSer. No. 11/613,851, filed Dec. 20, 2006, now U.S. Pat. No. 7,364,761,which is a continuation of U.S. patent application Ser. No. 10/952,322,filed Sep. 28, 2004, now abandoned, which is a continuation of U.S.patent application Ser. No. 10/678,025, filed Sep. 30, 2003, now U.S.Pat. No. 7,078,066, which is a continuation of U.S. patent applicationSer. No. 09/527,170, filed Mar. 16, 2000, now U.S. Pat. No. 6,627,233,which in turn is a continuation of PCT Application Serial No.PCT/US97/16731, filed Sep. 18, 1997, designating the United States, allof which are hereby incorporated by reference.

BACKGROUND OF THE INVENTION

The present invention relates to chewing gum compositions and methods ofproducing chewing gum. More particularly, the invention relates toproducing chewing gum containing physiological cooling agents.Preferably the physiological cooling agents are used in combination orhave been treated to control their release and enhance shelf lifestability. Also, the physiological cooling agents may be addedindividually or as part of a cooling flavor composition, or used inchewing gum coatings.

In recent years, efforts have been devoted to controlling releasecharacteristics of various ingredients in chewing gum. Efforts have beendirected at perfecting the use of high-intensity sweeteners within thechewing gum formulation, to thereby increase the shelf-life stability ofthe ingredients, i.e., the protection against degradation of thehigh-potency sweetener over time.

Patent Cooperation Treaty Publication No. 89-03170 discloses a method ofcontrolling the release of acesulfame K. In this process, the sweeteneris encapsulated fully or partially to modify the release rate in chewinggum.

Other patent publications disclose how a sweetener like aspartame can bephysically modified to control its release rate in chewing gum.

For example, U.S. Pat. No. 4,597,970 to Sharma et al. teaches a processfor producing an agglomerated sweetener wherein the sweetener isdispersed in a hydrophobic matrix consisting essentially of lecithin, aglyceride and a fatty acid or wax having a melting point between 25 and100° C. The disclosed method uses a spray congealing step to form thesweetener-containing matrix into droplets, followed by a fluid-bedsecond coating on the agglomerated particles.

U.S. Pat. Nos. 4,515,769 and 4,386,106, both to Merrit et al., teach atwo step process for preparing a delayed release flavorant for chewinggum. In this process, the flavorant is prepared in an emulsion with ahydrophilic matrix. The emulsion is dried and ground and the particlesare then coated with a water-impermeable substance.

U.S. Pat. No. 4,230,687 to Sair et al. teaches a process for encasing anactive ingredient to achieve gradual release of the ingredient in aproduct such as chewing gum. The described method involves adding theingredient to an encapsulating material in the form of a viscous paste.High shear mixing is used to achieve a homogeneous dispersion of theingredient within the matrix, which is subsequently dried and ground.

U.S. Pat. No. 4,139,639 to Bahoshy et al. teaches a process of “fixing”aspartame by co-drying (by spray drying or fluid bed coating) a solutioncontaining aspartame and an encapsulating agent, such as gum arabic, tothereby surround and protect the aspartame in the gum during storage.

U.S. Pat. No. 4,384,004 to Cea et al. teaches a method of encapsulatingaspartame with various solutions of encapsulating agents using variousencapsulation techniques, such as spray drying, in order to increase theshelf stability of the aspartame.

U.S. Pat. No. 4,634,593 to Stroz et al. teaches a method for producingcontrolled release sweeteners for confections, such as chewing gum. Themethod taught therein involves the use of an insoluble fat materialwhich is mix mulled with the sweetener.

Several known compounds have what can be characterized as a “cooling”activity, and are referred to in the art as “physiological coolingagents.” Physiological cooling agents are perceived as cold or cool whencontacted with the human body and, in particular, with the mucousmembranes of the mouth, nose and throat.

Efforts have been directed at perfecting the use of physiologicalcooling agents within chewing gum formulations to enhance flavorcomposition and control their release to enhance the flavor of chewinggum.

U.S. Pat. No. 5,326,574 discloses a process for codrying thephysiological cooling agent 3-l-menthoxypropane-1,2-diol with a foodacceptable, water-soluble carrier and mixing the resulting product intochewing gum.

Peppermint oil is currently used to create a “cooling” in oral productssuch as toothpaste, mouthwash, chewing gum, candy and other foodproducts. Peppermint oil generally comprises about 45% menthol, about20% menthone, about 5% menthyl acetate, about 5% eucalyptol and manyother constituents. Peppermint oil is even used in non-peppermintproducts, such as spearmint or wintergreen flavored products, in orderto create this desired cooling effect. However, peppermint notes arethen found in the resulting non-peppermint flavored products.

Menthol is also known for its physiological cooling effect on the skinand mucous membranes of the mouth. Being a major constituent ofpeppermint oil, menthol has been used extensively in foods, beverages,dentrifices, mouthwashes, toiletries, lotions and the like. Thedisadvantages of using menthol, however, are its strong minty odor andthe harsh notes it imparts to compositions in which it is found.

A need, therefore, exists for a cooling flavor composition that willcontribute a long-lasting cooling sensation to products in which it isfound without the unwanted harshness or flavor characteristics that comefrom adding menthol.

It would be desirable to provide a high flavor impact chewing gum thatdoes not manifest the harsh notes normally associated with some chewinggum. It would also be desirable to provide a clean, high-quality flavorchewing gum with a good cooling effect.

The present invention also relates to a coated chewing gum. Chewing gumsare frequently covered with hard or soft coatings. The coatings providean opportunity for the manufacturer to vary the taste, appearance,mouth-feel and nutritional value of the chewing gum.

For example, some consumers prefer a burst of intense flavor over theslow, gentle flavor release normally associated with chewing gum. Inorder to provide a favorable flavor impact, gum manufacturers have addedflavors to the coating of a coated chewing gum. These flavors includespearmint flavor, peppermint flavor, wintergreen flavor and fruitflavors. In addition, very strong flavors such as menthol have oftenbeen used to provide a burst of flavor. However, at concentrationseffective to provide a burst of flavor, menthol or mint flavors alsomanifest a bitter, harsh, burning taste (hereinafter “harsh notes”).

The harsh notes are particularly acute with sugarless gum. In the caseof coated gum with sugar, the sugar masks many of the harsh notes ofmenthol and mint flavors (although high levels of menthol or mintflavors can still manifest the harsh notes). However, recent efforts toproduce sugarless coated gums have highlighted the difficulties ofproviding an initial burst of flavor without the harsh notes associatedwith traditional flavoring.

One method to alleviate the problem of harsh notes in sugarless coatedchewing gum is the use of xylitol as a coating material. Xylitol has asweetness level equivalent to sugar, and produces a cooling effect dueto its endothermic heat of solvation. It produces a clean, high-qualityflavor with a good cooling effect, particularly when it is used withmenthol and mint flavors.

Coating with xylitol is described in U.S. Pat. No. 4,105,801; U.S. Pat.No. 4,127,677; U.S. Pat. No. 4,681,766; U.S. Pat. No. 4,786,511; andU.S. Pat. No. 4,828,845.

The disadvantage of xylitol is that it is an expensive ingredient. Manyefforts have been made to replace xylitol with a less expensivesugarless polyol. The most common and lowest cost polyol used in chewinggum is sorbitol. However, panning with sorbitol has been very difficultsince it is hygroscopic and does not readily crystallize.

A number of patents have been published that use various procedures tocoat with sorbitol, including G.B. Patent No. 2,115,672; U.S. Pat. No.4,317,838; and U.S. Pat. No. 4,753,790. A successful sorbitol hardcoating was reported in U.S. Pat. No. 4,423,086, particularly when thesorbitol was at least 99% D-sorbitol. However, the quality of coatingnever approached the quality of typical xylitol coatings.

Other coating patents that teach alternative polyols to xylitol include:U.S. Pat. No. 4,840,797, which discloses a maltitol coating whichrequired over 95% maltitol to obtain a good quality coating on pelletgum; U.S. Pat. Nos. 5,248,508 and 4,792,453, which disclose ahydrogenated isomaltulose coating; and U.S. Pat. No. 5,603,970, whichdiscloses an erythritol coating.

Still other patents teach partially replacing the xylitol with sorbitol,lactitol, or maltitol. However, these cannot be applied in the samesolution, but must be applied by alternating solutions. In other words,a solution of one polyol is applied, then another solution of anotherpolyol is applied. These patents include: U.S. Pat. No. 5,270,061; U.S.Pat. No. 5,376,389; PCT Application Nos. PCT/US93/09354 (published asWO95/08925); PCT/US94/10406 (published as WO95/07625); andPCT/US93/08730 (published as WO95/07622).

A booklet entitled “The Evaluation of Chewing Gum—Xylitol and thePrevention of Dental Caries” published in 1985 by Xyrofin describes acoating formed by panning with a solution containing xylitol and up to10% sorbitol. U.S. Pat. No. 5,536,511 discloses a coating that comprisesco-crystallized xylitol and erythritol. In an approach different frompanning from a solution, U.S. Pat. No. 4,146,653 discloses a moltenblend of xylitol and sorbitol that are used to form a coating.

U.S. Pat. No. 5,409,715 discloses coating chewing gum with variousmaterials, including waxes, lipids, fatty acids, fats, oils, cellulosederivatives, modified starch, dextrin, gelatin, zein, vegetable gums,proteins, edible polymers, edible plastic film, maltodextrins, polyols,low calorie carbohydrate bulking agents, shellac and combinationsthereof.

It would be desirable to provide a high flavor impact chewing gumcoating that does not manifest the harsh notes normally associated withsuch coatings. It would also be desirable to provide a clean,high-quality flavor coated chewing gum with a good cooling effect, whilereducing or eliminating the xylitol currently preferred in sugarlesscoatings.

SUMMARY OF THE INVENTION

This invention incorporates a physiological cooling agent or combinationof physiological cooling agents into a chewing gum. One preferredembodiment of the invention provides a chewing gum having a clean, coolsensation imparted by a cooling flavor composition that includes aphysiological cooling agent. Another preferred embodiment also containsa flavor, and a combination of physiological cooling agents which havebeen treated so as to modify their release from the chewing gum. Theresult is a synergy between the physiological cooling agents and theflavor, which provides a high flavor impact at a lower concentration offlavor. Thus, with either or both aspects of the present invention,chewing gum can be made with a long lasting cooling sensation withoutunwanted harshness or flavor characteristics. The gum may have a highflavor impact, as well as a clean, high quality flavor with good coolingeffect.

In the first aspect, applicants have discovered that using menthol andmenthone in combination with one or more physiological cooling agentsprovides optimal cooling without unwanted flavor characteristics. Addingthe physiological cooling agent provides the chewing gum with anunexpected, high-flavor impact where the harsh notes have been reducedor eliminated. This is particularly valuable for sugarless chewing gumwhere the harsh notes of the flavor are not masked by sugar.

In this first aspect, the invention is directed to cooling flavorcompositions that provide the desired “cooling” sensation but not theunwanted harshness and flavor characteristics. The cooling flavorcompositions of the present invention replace some or all of thepeppermint oil presently used to create a “cooling.” Because the coolingflavor compositions use menthol and menthone, as opposed to peppermintoil, the cooling flavor compositions do not add unwanted peppermintnotes.

In addition, the physiological cooling agent provides a coolingsensation similar to that associated with gum made from xylitol.Consequently, a lower cost polyol can be used as a chewing gum materialwithout sacrificing the clean, high-quality, cooling sensationordinarily associated with xylitol.

In one embodiment, the invention is a cooling flavor compositioncomprising:

-   -   a) about 40% to about 80% by weight menthol;    -   b) about 15% to about 50% by weight menthone; and    -   c) about 3% to about 25% by weight of at least one physiological        cooling agent selected from the group consisting of menthyl        succinate; acyclic carboxamide; menthyl lactate;        3-l-menthoxypropane-1,2-diol; N-substituted p-menthane        carboxamide; menthone glycerol ketals and mixtures thereof.

In another embodiment, the invention is an oral composition, such aschewing gum, comprising a flavor and a cooling flavor compositioncomprising:

-   -   a) about 40% to about 80% by weight menthol;    -   b) about 15% to about 50% by weight menthone; and    -   c) about 3% to about 25% by weight of at least one physiological        cooling agent selected from the group consisting of menthyl        succinate; acyclic carboxamide; menthyl lactate;        3-l-menthoxypropane-1,2-diol; N-substituted p-menthane        carboxamide; menthone glycerol ketals and mixtures thereof.

In this embodiment, the cooling flavor compositions are used in chewinggum to improve the “cool” sensation perceived upon chewing the gum andto extend the duration of the “cool” sensation.

In other embodiments of the invention, the cooling flavor compositionsmay also be used in other comestibles or even topical products such ascreams and lotions.

In a second aspect, the present invention also includes a method forproducing chewing gum with an acyclic carboxamide physiological coolingagent or combinations of physiological cooling agents, treated to have amodified-release. The controlled release combination of physiologicalcooling agents is obtained by modifying the cooling agents byencapsulation, partial encapsulation or partial coating, entrapment orabsorption with water-soluble materials or water-insoluble materials.The procedures for modifying the physiological cooling agents includespray drying, spray chilling, fluid-bed coating, coacervation,extrusion, and other agglomerating and standard encapsulatingtechniques. The cooling agents may also be absorbed onto an inert orwater-insoluble material. The cooling agents may be modified in amultiple step process comprising any of the processes noted.

The combination of cooling agents, or the combination of cooling agentswhen modified according to the present invention, give a chewing gum acontrolled-release cooling agent. A higher quantity of cooling agentscan be used without resulting in a high initial cooling agent impact,but instead having a delayed cooling release in chewing gum, giving ahighly consumer-acceptable chewing gum product. Some cooling agents havea very slow release, but may be modified to give a fast release for moreinitial impact.

Another embodiment of this invention incorporates a physiologicalcooling agent into the coating of a coated chewing gum. One preferredembodiment of the invention provides a chewing gum coating having aclean, cool sensation in which xylitol is replaced, in part or in whole,by a less expensive coating material.

Another preferred embodiment also contains a flavor, where the synergybetween the physiological cooling agent and the flavor provides a highflavor impact at a lower concentration of flavor. Adding thephysiological cooling agent provides the coated chewing gum with anunexpected, high-flavor impact where the harsh notes have been reducedor eliminated. This is particularly valuable for sugarless chewing gumwhere the harsh notes of the flavor are not masked by sugar.

In addition, the physiological cooling agent provides a coolingsensation similar to that associated with coatings made from xylitol.Consequently, a lower cost polyol can be used as a chewing gum coatingmaterial without sacrificing the clean, high-quality, cooling sensationordinarily associated with xylitol coatings.

In yet another aspect of the invention, a chewing gum compositioncomprises an acyclic carboxamide physiological cooling agent and eithermenthol or another physiological cooling agent, or both.

In still another embodiment, a chewing gum composition comprises a hotflavor, such as cinnamon, and a physiological cooling agent. Thisembodiment produces a breath freshness perception.

The foregoing and other features and advantages of the present inventionwill become apparent from the following detailed description of thepresently preferred embodiments, when read in conjunction with theaccompanying examples.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a graph showing a rating of perception of fresh breath overtime after chewing comparative and inventive gum samples.

FIG. 2 is a graph showing a rating of perceived breath odor over timeafter chewing comparative and inventive gum samples.

FIG. 3 is a graph showing a rating of perceived effectiveness for breathfreshening over time after chewing comparative and inventive gumsamples.

DETAILED DESCRIPTION OF THE PRESENTLY PREFERRED EMBODIMENTS OF THEINVENTION

In the context of this invention, chewing gum refers to chewing gum,bubble gum and the like. Moreover, all percentages are based on weightpercentages unless otherwise specified. Further, although some terms arereferred to in the singular, it is understood that such references mayalso encompass the plural. For example, although chewing gum coating isreferred to in the singular, it is understood that coated chewing gumnormally contains multiple layers of coating. Therefore a phrase thatrefers to “the coating,” refers to one or more layers of coating.Finally, all references cited herein are incorporated by reference.

The composition of a chewing gum tends to suppress the release of itsflavors. Although a slow flavor release is desirable in many instances,some consumers prefer a burst of intense flavor. One method to provide achewing gum with a greater flavor impact is the addition of encapsulatedflavor to a chewing gum. For example, for a cool and refreshing taste,cooling flavors such as encapsulated menthol and/or mint flavors areadded to chewing gum. A menthol/mint combination is disclosed in U.S.Pat. No. 4,724,151.

However, the improved flavor impact of adding cooling flavors to thechewing gum is somewhat offset by the disadvantage of the bitter, harsh,burning sensations associated with high concentrations of such flavors.This disadvantage is particularly acute for sugarless gum, since sugartends to mask the harsh notes.

The inventors have found that adding a combination of physiologicalcooling agents or a combination of cooling agents that have a modifiedrelease from the chewing gum provides a favorable flavor impact. As aresult, the inventors are able to reduce or eliminate the harsh notesassociated with the prior art high flavor-impact chewing gums, even inthe case of sugarless chewing gums.

By adding a combination of physiological cooling agents to a menthol ormint type flavored chewing gum, one can obtain a strong cooling andclean minty flavor, without the higher concentrations of menthol or mintflavors required in the prior art. Also, the fast release encapsulationof a combination of physiological cooling agents complement the mintflavors to give a high impact of flavor and cooling normally found inchewing gum. This cooling effect is like menthol cooling, but withoutthe bitterness associated with menthol.

For sugarless gums, chewing gums containing xylitol have become verypopular because xylitol has about the same sweetness level as sugar anda cooling ability due to its endothermic heat of salvation. With thissweetness, xylitol masks the harsh notes of high impact flavors such asmenthol and mint flavors. At the same time, its cooling effectcomplements the cooling effect of the cooling flavors. As a result,xylitol provides a clean, high-quality cooling effect. Xylitol incombination with physiological cooling agents give chewing gum a highquality flavor profile with good cooling. However, because of itsexpense, various efforts have been made to replace xylitol in coatingswith a less expensive ingredient, such as another polyol.

Another method to provide a chewing gum with a greater flavor impact isthe addition of flavor to the coating of a coated chewing gum. Forexample, for a cool and refreshing taste, cooling flavors such asmenthol and/or mint flavors are added to the coating of chewing gum.

However, the improved flavor impact of adding cooling flavors to thechewing gum coating is somewhat offset by the disadvantage of thebitter, harsh, burning sensations associated with high concentrations ofsuch flavors. This disadvantage is particularly acute for sugarless gum,since sugar tends to mask the harsh notes.

The inventors have found that adding a physiological cooling agent tothe coating provides a favorable flavor impact. As a result, theinventors are able to reduce or eliminate the harsh notes associatedwith the prior art high flavor-impact coated chewing gums, even in thecase of sugarless, coated chewing gums.

By adding a physiological cooling agent to a menthol or mint typeflavored chewing gum coating, one can obtain a strong cooling and cleanminty flavor, without the higher concentrations of menthol or mintflavors required in prior art coatings. Also, the physiological coolingagents complement the mint flavors to give a high impact of flavor andcooling normally found in coated chewing gum. This cooling effect islike menthol cooling, but without the bitterness associated withmenthol.

Coated chewing gums of the present invention may be made with a varietyof chewing gum compositions. The chewing gum is prepared as conventionalchewing gum, but formed into pellets or balls. The pellets/balls canthen be coated by a variety of methods known in the art, such asconventional panning methods to coat chewing gum. The coating isgenerally applied in multiple layers, where the composition of one layeris not necessarily the composition of the other layers.

The coating of the present invention contains at least a coatingmaterial and a physiological cooling agent. It may also contain otheringredients such as flavors, artificial sweeteners and dispersingagents, coloring agents, film formers and binding agents.

Coating material constitutes the substantial portion of the chewing gumcoating. Examples of coating material include sugars such as sucrose,maltose, dextrose and glucose syrup; polyols such as maltitol, lactitol,xylitol, mannitol, erythritol, sorbitol, hydrogenated isomaltulose andhydrogenated starch hydrolysates; and combinations thereof.

For sugarless gums, xylitol coatings have become very popular becausexylitol has about the same sweetness level as sugar and a coolingability due to its endothermic heat of salvation. With this sweetness,xylitol masks the harsh notes of high impact flavors such as menthol andmint flavors. At the same time, its cooling effect complements thecooling effect of the cooling flavors. As a result, xylitol provides aclean, high-quality cooling effect. When used with physiological coolingagents, a synergistic cooling effect may be noted with xylitol. However,because of its expense, various efforts have been made to replacexylitol in coatings with a less expensive ingredient, such as anotherpolyol.

One problem with polyol substitutes for xylitol is that they aregenerally much less sweet than xylitol or sugar. In the presence of highlevels of flavor, the polyol substitutes generally provide a coatedproduct with a bitter, unpleasant taste. To some degree, high intensitysweeteners may be used to counteract bitterness, but these also may havesome objectionable taste. Also, some of these polyols themselves maycontribute to a bitter taste.

By using physiological cooling agents in a coating that comprisespolyols other than xylitol, the coating manifests a cooling similar toxylitol cooling. Thus xylitol substitutes, which cost significantly lessthan xylitol, can be used to coat gum and give a taste sensation similarto xylitol.

Many of the coating material references cited above contemplate theaddition of one or more flavors to chewing gum coating. However, nonedisclose the addition of a physiological cooling agent to give thecoating a cooling sensation like that of xylitol.

By using a combination of physiological cooling agents treated to have amodified release in a chewing gum that comprises polyols other thanxylitol, the effect is a cooling similar to xylitol cooling. Thusxylitol substitutes, which cost significantly less than xylitol, can beused in gum and give a taste sensation similar to xylitol.

Physiological cooling agents encompasses any number of physiologicalcooling agents. However, in the context of this invention, the term“physiological cooling agent” does not include traditionalflavor-derivatives such as menthol or menthone. Preferred physiologicalcooling agents do not have a perceptible flavor of their own, but simplyprovide a cooling effect.

Since the physiological cooling agents do not have their own perceptibleflavor, they can be used with other types of flavors to offer new andunique advantages, such as breath freshening. Most confectioneryproducts which are promoted for breath freshening are mint flavoredproducts which contain moderate to high levels of menthol. Menthol is acomponent of peppermint oil which has a cooling property which providesto the consumer a perception of freshness in the oral cavity.

Paradoxically, some cinnamon flavored products have also been marketedfor breath freshening based on the physiological heating provided bycinnamic aldehyde and other spice flavor components. In some cases,menthol or peppermint oil has been added to cinnamon flavored productsto provide a cooling sensation and enhance breath freshening. While someconsumers enjoy the presence of a mint note in cinnamon confections,others describe the flavor as “muddy”, “dirty” and “confused”,preferring a “pure” cinnamon flavor.

Another embodiment of the present invention is a confectionery product,preferably a chewing gum, which incorporates a spicy hot flavor, issubstantially free of menthol and other mint oil components and whichcomprises a physiological cooling agent which imparts improved breathfreshening and a desirable hot/cold sensory perception without a mintflavor.

It has surprisingly been found that many consumers, who may notappreciate the addition of mint flavor to cinnamon flavored candies andchewing gums, do enjoy the addition of a non-menthol, physiologicalcooling agent in such products. Furthermore, it has been found that theinventive products have greatly enhanced breath freshening propertiescompared to cinnamon flavored confections without physiological coolingagents.

The confectionery products of this embodiment of the invention can beany new or existing type of product in that category. Hard candies, hardor soft pan coated items, chewy confections and powdered candies arespecifically contemplated. Chewing gum is a preferred embodiment.

The confections of this embodiment of the invention will include anatural or non-menthol hot spice flavor such as cinnamon, clove, ginger,black pepper, cayenne pepper and mixtures of these. Cinnamon flavor ispreferred. The flavor composition will be substantially free of mentholand mint oils. By substantially free, it is meant that the flavorcomposition will comprise less than about 15% and preferably less than10% of mint components. Most preferably, the flavor composition willhave 0% to 3% of mint components. The flavor composition will alsocontain a physiological cooling agent in an amount sufficient to impartnoticeable cooling to the product.

While there are references that disclose the use of physiologicalcooling agents in chewing gum and other confections, unique combinationsand controlled release are new areas of interest. Also, no referencesdisclose the use of physiological cooling agents in a chewing gumcoating. Because a flavor imparts a distinct and unique sensation whenit is used in a chewing gum, some combinations of the physiologicalcooling agents offer unique advantages and may be combined with varioustypes of flavors or with various methods of encapsulation and entrapmentfor controlled release.

Several U.S. and foreign references disclose specific compounds andclasses of compounds that are physiological cooling agents that may beused in the present invention. Some of these disclose the use ofphysiological cooling agents in chewing gum. These include:

U.S. Pat. No. 5,451,404 (a ketal combined with another coolant (mentholor carboxamides));

U.S. Pat. No. 5,372,824 (physiological cooling agents and reducedmenthol);

U.S. Pat. No. 5,348,750 (menthone ketals);

U.S. Pat. No. 5,326,574 (a spray dried 3-l-menthoxypropane-1,2-diol);

U.S. Pat. No. 5,266,592 (menthone glycerol ketals);

U.S. Pat. No. 5,165,943 (a cyclodextrin complex with physiologicalcooling agents);

U.S. Pat. No. 5,009,893 (p-menthane carboxamide physiological coolingagent with menthol for reduced bitterness);

U.S. Pat. No. 4,459,425 (3-l-menthoxypropane-1,2-diol);

U.S. Pat. No. 4,296,093 (substituted cyclohexanamides);

U.S. Pat. Nos. 4,248,859 and 4,318,900 (alkyl substituted alicycliccarboxylic acids, esters or amides);

U.S. Pat. Nos. 4,157,384 and 4,029,759 (various 3-substitutedp-menthanes);

U.S. Pat. No. 4,081,480 (alpha-oxy(oxo)mercaptan alkanes);

U.S. Pat. No. 4,070,449 (sulphoxides and sulphones);

U.S. Pat. Nos. 4,060,091; 4,190,643 and 4,136,163 (substitutedp-menthane-3-carboxamides);

U.S. Pat. Nos. 4,153,679; 4,296,255 and 4,230,688 (acycliccarboxamides);

U.S. Pat. No. 4,034,109 (acyclic sulphonamides and sulphinamides);

U.S. Pat. No. 4,033,994 (p-menthane-3-carboxylates);

U.S. Pat. Nos. 3,793,446 and 3,644,613 (ketoesters of menthol);

U.S. Pat. No. 3,720,762 (spilanthol with menthol or peppermint oil);

Canadian Patent No. 2,101,790 (carbonic acids having free polar groups);

German Patent No. 2,608,226 (menthyl lactate);

German Patent No. 2,433,165 (N-acetylglycine menthyl ester);

French Patent No. 2,577,922 (L-menthyl-3-hydroxybutyrate);

Japanese Patent No. 94/065023 (2-isopropenyl-5-methylcyclohexanol);

Great Britain U.S. Pat. No. 1,502,680 (bicyclic acids, esters, amidesand substituted menthanols);

Great Britain U.S. Pat. No. 1,476,351 (cyclic and acyclic amides, ureasand sulphonamides);

Great Britain U.S. Pat. No. 1,442,998 (trialkyl-substituted cyclohexanecarboxamides);

Great Britain Patents Nos. 1,421,744 and 1,421,743 (novel amides);

Great Britain U.S. Pat. No. 1,411,786 (cyclohexanamides);

Great Britain U.S. Pat. No. 1,404,596 (acyclic secondary and tertiaryalkanols);

PCT Publication No. WO 97/07771 (menthyl succinate and carboxamides);

PCT Publication No. WO 96/28133 (coolant composition for comestibles);

PCT Publication No. WO 96/17524 (a cooling composition comprisingN-substituted p-menthane carboxamides and menthol);

PCT Publication No. WO 94/010117 (cyclohexanol derivatives); and

U.S. Pat. No. 3,639,569 (physiological cooling agents).

Particular examples of physiological cooling agents include:

-   -   1) substituted p-menthanes, substituted p-menthane-carboxamides        (e.g., N-ethyl-p-menthane-3-carboxamide (FEMA 3455)), acyclic        carboxamides, substituted cyclohexanamides, substituted        cyclohexane carboxamides, substituted ureas and sulphonamides,        and substituted menthanols (all from Wilkinson Sword);    -   2) hydroxymethyl and hydroxyethyl derivatives of p-menthane        (from Lever Bros.);    -   3) menthyl succinate;    -   4) 2-mercapto-cyclo-decanone (from International Flavors and        Fragrances);    -   5) 2-isopropanyl-5-methylcyclohexanol (from Hisamitsu        Pharmaceuticals, hereinafter “isopregol”);    -   6) hydroxycarboxylic acids with 2-6 carbon atoms;    -   7) menthone glycerol ketals (FEMA 3807, tradename FRESCOLAT™        type MGA);    -   8) 3-l-menthoxypropane-1,2-diol (from Takasago, FEMA 3784,        (hereinafter “TCA”));    -   9) menthyl lactate; (from Haarman & Reimer, FEMA 3748, tradename        FRESCOLAT™ type ML).

While any of the above-disclosed physiological cooling agents may beused in chewing gum, the presently preferred physiological coolingagents are.

-   -   1) substituted p-menthane carboxamides (PMC), such as those        disclosed in U.S. Pat. Nos. 4,060,091; 4,190,643 and 4,136,163,        all assigned to Wilkinson Sword, especially        N-ethyl-p-menthane-3-carboxamide (called WS-3);    -   2) acyclic carboxamides (AC), such as those disclosed in U.S.        Pat. Nos. 4,296,255; 4,230,688; and 4,153,679: all assigned to        Wilkinson Sword, especially N-2,3-trimethyl-2-isopropyl        butanamide (called WS-23);    -   3) menthone glycerol ketal (MGK);    -   4) menthyl lactate (ML);    -   5) menthyl succinate (MS); and    -   6) 3-l-menthoxypropane-1,2-diol (TCA).

The concentration of physiological cooling agent will depend on theintensity of the physiological cooling agent and the desired coolingeffect. In general the concentration of cooling agents used is betweenabout 0.001% and about 2% by weight of the chewing gum. The preferredconcentration of cooling agent is between about 0.01% and about 1.0%,more preferably between 0.02% and about 0.5%.

The present invention contemplates that two or more physiologicalcooling agents may be added to the flavor used to make the chewing gum.On the other hand, the flavor and cooling agents may be added separatelyanywhere within the manufacturing process for making a chewing gumproduct.

These flavors include any flavor which is of food acceptable qualitycommonly known in the art such as essential oils, synthetic flavors ormixtures thereof. Such flavors include, but are not limited to, oilsderived from plants and fruits such as citrus oils, fruit essences,peppermint oil, spearmint oil, eucalyptus, other mint oils, clove oil,oil of wintergreen, cinnamic aldehyde, anise and the like. Flavors thatare very strong, such as menthol flavors, are also contemplated in thisinvention. Preferred flavors include cooling flavors such as peppermint,eucalyptus, menthol, wintergreen and fruity-mint; non-cooling flavorssuch as spearmint and cinnamon; and combinations thereof.

Artificial flavor components are also contemplated by the presentinvention. Those of ordinary skill in the art will recognize thatnatural and artificial flavors may be combined in any sensoriallyacceptable blend. All such flavors and blends are contemplated by thepresent invention.

The flavor may be added to the chewing gum formula in an amount suchthat it will contain from about 0.1% to about 10% flavor, preferablyfrom about 0.2% to about 3.0% flavor, and most preferably about 0.5% toabout 2% flavor.

For menthol flavored chewing gum, a combination of physiological coolingagents allows for a reduced overall concentration of menthol. However,it does not completely eliminate menthol, because menthol has a veryidentifiable unique taste and cooling sensation. Hence, in the case ofmenthol flavor, the physiological cooling agents only enhance thecooling while reducing the menthol bitterness.

The present invention thus is also directed to novel cooling flavorcompositions comprising menthol and menthone that contribute along-lasting cool sensation. These cooling flavor compositions may besubstituted for peppermint oil in non-peppermint products, resulting inadded coolness without harshness or unwanted flavor characteristics.They can, of course, also be used in peppermint flavored products.

It has been discovered that menthol, when used in conjunction withmenthone, provides a cool sensation without the characteristically harshtones of menthol. It has been further discovered that the use of mentholand menthone in combination with a physiological cooling agent resultsin a cooling flavor composition that provides initial optimal cooling,as well as extended coolness. The presence of only one of thesecomponents will not provide the desired results.

Menthol, which occurs naturally in peppermint oil, is the agent thatprovides the “cooling” sensation, but menthol alone tends to distortflavor notes. When used in conjunction with menthone, however, theresult is cooling without harshness because the menthone helps to curbthe harsh qualities of the menthol.

In one embodiment of the present invention, menthol and menthone areused in conjunction with one or more physiological cooling agents toproduce a cooling flavor composition yielding optimal coolness. Thementhol and menthone are used in their separated, or pure, form, asdistinguished from being present in peppermint oil. Used as such, thementhol and menthone supply a fast release of the “cooling” sensationbut do not add a peppermint flavor. These cooling flavor compositions,which have a physiological cooling effect, can be used in food, drinks,dentrifices, gargles, cosmetics, lotions, etc. Suitable physiologicalcooling agents that are preferred in this aspect of the invention arementhyl succinate; menthyl lactate; 3-l-menthoxypropane-1,2-diol;menthone glycerol ketals; N-substituted p-menthane carboxamide; acycliccarboxamide and mixtures thereof. The preferred cooling agents arementhyl succinate, N-substituted p-menthane carboxamide (WS-3), acycliccarboxamide (WS-23) and menthyl lactate.

The cooling flavor composition comprising menthol, menthone and one ormore physiological cooling agents is more potent than peppermint oilalone. As a result, less of the cooling blend is needed to achieve thedesired coolness than peppermint oil. This would decrease the need forpeppermint oil, a costly commodity which has an uncertain supply, savingmoney and conserving peppermint oil. However, if desired, peppermint oilmay be added in addition to the cooling flavor compositions of thepresent invention.

In another embodiment, the cooling flavor composition comprisingmenthol, menthone and one or more physiological cooling agents is usedin oral compositions such as chewing gum. The result is oralcompositions having optimal cooling without harsh tones or unwantedflavor characteristics. Moreover, the blend of menthol, menthone and oneor more synthetic cooling agents extends the coolness of the oralcompositions in which the blend is used. This novel blend supplies afast release of the cooling sensation from the menthol and menthone, andan extended release from the physiological cooling agents.

Because the cooling flavor compositions of the present invention willnot impart an unwanted peppermint flavor to non-peppermint products,these compositions may be used to add coolness to fruit and otherflavors.

Physiological cooling agents generally release slowly from chewing gumduring the early stages of mastication of the gum because of their lowsolubility in water. However, some like TCA are moderately fast release,others like WS-3, WS-23 are moderately slow release, and others likementhone glycerol ketal, menthyl lactate and menthyl succinate are veryslow release.

Combinations of cooling agents may not only be synergistic but may alsoprovide both moderate release and slow release to give flavor impact andflavor extension. Physical modifications of the physiological coolingagents by encapsulation with another substrate will also modify theirrelease in chewing gum by modifying the solubility or dissolution rate.Any standard technique which gives partial or full encapsulation of thecombination of physiological cooling agents can be used. Thesetechniques include, but are not limited to, spray drying, spraychilling, fluid-bed coating, and coacervation. These encapsulationtechniques that give partial encapsulation or full encapsulation can beused individually or in any combination in a single step process ormultiple step process. Generally, a modified release of physiologicalcooling agents is obtained in multistep processes like spray drying thecombined physiological cooling agents and then fluid-bed coating theresultant powder.

The encapsulation techniques here described are standard coatingtechniques and generally give varying degrees of coating from partial tofull coating, depending on the coating composition used in the process.Also, the coating compositions may be susceptible to water permeation tovarious degrees. Generally, compositions that have high organicsolubility, good film forming properties and low water solubility givebetter delayed release of the physiological cooling agents. Suchcompositions include acrylic polymers and copolymers, carboxyvinylpolymer, polyamides, polystyrene, polyvinyl acetate, polyvinyl acetatephthalate, polyvinyl pyrrolidone and waxes. Although all of thesematerials are possible for encapsulation of physiological coolingagents, only food grade materials should be considered. Two standardfood grade coating materials that are good film formers but not watersoluble are shellac and Zein. Others which are more water soluble, butgood film formers, are materials like agar, alginates, a wide range ofcellulose derivative like ethyl cellulose and hydroxypropylmethylcellulose, dextrin, gelatin and modified starches. These ingredients,which are generally approved for food use, may give a faster releasewhen used as an encapsulant for the physiological cooling agents. Otherencapsulants like acacia or maltodextrin can also encapsulate thephysiological cooling agents, but give a faster release rate of thephysiological cooling agents.

The amount of coating or encapsulating material on the cooling agentsalso controls the length of time for their release from chewing gum.Generally, the higher the level of coating and the lower the amount ofactive cooling agents, the slower the release of the cooling agentsduring mastication. To obtain the desired cooling agent release to blendwith a gum's flavor release, the encapsulant should be a minimum ofabout 20% of the coated cooling agents. Preferably, the encapsulantshould be a minimum of about 30% of the coated cooling agents, and mostpreferably should be a minimum of about 40% of the coated coolingagents. Depending on the coating material, a higher or lower amount ofcoating material may be needed to give the desired release of coolingagents.

Another method of giving a delayed release of the physiological coolingagents is agglomeration with an agglomerating agent which partiallycoats the cooling agents. This method includes the step of mixing thecooling agents and agglomerating agent with a small amount of water orsolvent. The mixture is prepared in such a way as to have individual wetparticles in contact with each other so a partial coating can beapplied. After the water or solvent is removed, the mixture is groundand used as a powdered coated cooling agent.

Materials that can be used as the agglomerating agent are the same asthose used in the encapsulation mentioned previously. However, since thecoating is only a partial encapsulation, some agglomeration agents aremore effective in delaying release than others. Some of the betteragglomerating agents are the organic polymers like acrylic polymer andcopolymers, polyvinyl acetate, polyvinyl-pyrrolidone, waxes, shellac andZein. Other agglomerating agents are not as effective in giving adelayed release as are the polymers, waxes, shellac and Zein, but can beused to give some delayed release. These others agglomerating agentsinclude, but are not limited to, agar, alginates, a wide range ofcellulose derivatives, dextrin, gelatin, modified starches, andvegetable gums like guar gums, locust bean gum, and carrageenan. Eventhough the agglomerated cooling agents are only partially coated, whenthe quantity of coating is increased compared to the quantity of thecooling agents, the release can be delayed for a longer time duringmastication. The level of coating used in the agglomerated product is aminimum of about 5%. Preferably the coating level is a minimum of about15%, and more preferably about 20%. Depending on the agglomeratingagent, a higher or lower amount of agent may be needed to give thedesired release of cooling agents.

The physiological cooling agents may be coated in a two-step process ormultiple step process. The physiological cooling agents may beencapsulated with any of the materials as described previously and thenthe encapsulated material can be agglomerated as described previously toobtain an encapsulated/agglomerated product that could be used inchewing gum to give a delayed release.

In another embodiment of this invention, the physiological coolingagents may be absorbed onto another component, often referred to as acarrier, which is porous and become entrapped in the matrix of theporous component. Common materials used for absorbing the physiologicalcooling agents include, but are not limited to, silicas, silicates,pharmasorb clay, sponge-like beads or microbeads, amorphous carbonatesand hydroxides, including aluminum and calcium lakes, vegetable gums andother spray dried materials.

Depending on the type of absorbent material and how it is prepared, theamount of the physiological cooling agents that can be loaded onto theabsorbent will vary. Generally materials like polymers or spongelikebeads or microbeads, amorphous sugars, and alditols and amorphouscarbonates and hydroxides absorb about 10% to about 40% of the weight ofthe absorbent. Other materials like silicas and pharmasorb clays may beable to absorb about 20% to about 80% of the weight of the absorbent.

The general procedure for absorbing the physiological cooling agentsonto the absorbent is as follows. An absorbent like fumed silica powdercan be mixed in a powder blender and a solution of the physiologicalcooling agents can be sprayed onto the powder as mixing continues. Thesolution can be about 5% to 30% cooling agent, and higher levels may beused if higher temperatures are used. Generally water is the solvent,but other solvents like alcohol should also be used if approved for usein food. As the powder mixes, the liquid is sprayed onto the powder.Spraying is stopped before the mix becomes damp. The still flowingpowder is removed from the mixer and dried to remove the water or othersolvent, and ground to a specific particle size.

After the physiological cooling agents are absorbed onto an absorbent orfixed onto an absorbent, the fixative/cooling agents can be coated byencapsulation. Either full or partial encapsulation may be used,depending on the coating composition used in the process. Fullencapsulation may be obtained by coating with a polymer as in spraydrying, spray chilling, fluid-bed coating, extrusion, coacervation, orany other standard technique. A partial encapsulation or coating can beobtained by agglomeration of the fixative/cooling agents mixture usingany of the materials discussed above.

The physiological cooling agents can be treated to modify their releaseby being entrapped in an extrusion process. Examples of such extrusionprocesses are disclosed in U.S. Pat. No. 5,128,155 and PCT PublicationNo. WO 94/06308.

The four methods to use to obtain a modified release of physiologicalcooling agents are (1) encapsulation by spray drying, fluid-bed coating,spray chilling and coacervation to give full or partial encapsulation;(2) agglomeration to give partial encapsulation; (3) fixation orabsorption which also gives partial encapsulation; and (4) entrapment byextrusion. These four methods, combined in any usable manner whichphysically isolates the physiological cooling agents, modifies theirdissolvability or modifies the release of physiological cooling agentsare included in this invention.

The previously described cooling flavor compositions and encapsulated,agglomerated or absorbed physiological cooling agents may readily beincorporated into a chewing gum composition. Generally the physiologicalcooling agents will be added to the gum in either the form of a coolingflavor composition or as part of a modified release combination ofphysiological cooling agents. However, both of these aspects of theinvention may be used in the same gum formula, and the cooling flavorcomposition itself or its individual components may be treated to have amodified release. The remainder of the chewing gum ingredients arenoncritical to the present invention. That is, the cooling flavorcomposition and/or coated particles of physiological cooling agents canbe incorporated into conventional chewing gum formulations in aconventional manner. Naturally, the preferred chewing gum formulation isa sugarless formulation. However, the physiological cooling agents mayalso be used in a sugar chewing gum. The cooling flavor composition andcoated physiological cooling agents may be used in either regularchewing gum or bubble gum.

In other embodiments of this invention, particularly coatings of chewinggum, the concentration of physiological cooling agent will depend on theintensity of the physiological cooling agent and the desired coolingeffect. In general the concentration of cooling agents used is betweenabout 0.001% and about 1% by weight of coating. The preferredconcentration of cooling agent is between about 0.01% and about 0.5%,more preferably between about 0.02% and about 0.2%.

The present invention contemplates that one or more flavors may be addedto the syrup used to make the coating, or applied to the gum centerwhile the syrup coating is drying, or after the coating has dried.Furthermore, the flavor may be applied anywhere within the sequence ofcoats, for example, after the third, twelfth, eighteenth, etc., coats.

These flavors include any flavor which is of food acceptable quality,including the flavors described earlier for use in chewing gum. Theflavor may be added to the coating syrup in an amount such that thecoating will contain from about 0.2% to about 1.2% flavor and preferablyfrom about 0.7% to about 1.0% flavor.

For menthol flavored coatings, this concentration of physiologicalcooling agent allows a reduced overall concentration of menthol.However, it does not completely eliminate menthol, because menthol has avery identifiable unique taste and cooling sensation. Hence, in the caseof menthol flavor, the physiological cooling agents only enhance thecooling while reducing the menthol bitterness.

Artificial sweeteners contemplated for use in the coating include butare not limited to synthetic substances, saccharin, thaumatin, alitame,saccharin salts, aspartame, sucralose and acesulfame-K. The artificialsweetener may be added to the coating syrup in an amount such that thecoating will contain from about 0.05% to about 0.3%, and preferably fromabout 0.10% to about 0.15% artificial sweetener.

Dispersing agents are often added to syrup coatings for the purpose ofwhitening and tack reduction. Dispersing agents contemplated by thepresent invention to be employed in the coating syrup include titaniumdioxide, talc, or any other antistick compound. Titanium dioxide is apresently preferred dispersing agent of the present invention. Thedispersing agent may be added to the coating syrup in amounts such thatthe coating will contain from about 0.1% to about 1.0%, and preferablyfrom about 0.3% to about 0.6% of the agent.

Coloring agents are preferably added directly to the syrup in the dye orlake form. Coloring agents contemplated by the present invention includefood quality dyes. Film formers preferably added to the syrup includemethyl cellulose, gelatins, hydroxypropyl cellulose, ethyl cellulose,hydroxyethyl cellulose, carboxymethyl cellulose and the like andcombinations thereof. Binding agents may be added either as an initialcoating on the chewing gum center or may be added directly into thesyrup. Binding agents contemplated by the present invention include gumarabic, alginate, cellulosics, vegetable gums and the like.

Conventional panning procedures generally use sucrose as the coatingmaterial, but recent advances in panning have allowed the use of othercarbohydrate materials to be used in the place of sucrose. Some of thesecomponents include, but are not limited to, dextrose, maltose,erythritol, xylitol, hydrogenated isomaltulose, maltitol and other newpolyols or a combination thereof.

The coating material may be blended with panning modifiers including,but not limited to, gum arabic, maltodextrins, corn syrup, gelatin,cellulose type materials like carboxymethyl cellulose or hydroxymethylcellulose, starch and modified starches, vegetable gums like alginates,locust bean gum, guar gum and gum tragacanth, insoluble carbonates likecalcium carbonate or magnesium carbonate, and talc. Antitack agents mayalso be added as panning modifiers, which allow the use of a variety ofcarbohydrates and sugar alcohols to be used in the development of newpanned or coated gum products.

The chewing gum center of the present invention follows the generalpattern outlined below. These centers may contain physiological coolingagents as an ingredient.

In general, a chewing gum center composition or other chewing gumcompositions typically contain a chewable gum base portion which isessentially free of water and is water-insoluble, a water-soluble bulkportion and flavors which are typically water insoluble. Thewater-soluble portion dissipates with a portion of the flavor over aperiod of time during chewing. The gum base portion is retained in themouth throughout the chew.

The insoluble gum base generally comprises elastomers, elastomersolvents, plasticizers, waxes, emulsifiers and inorganic fillers.Plastic polymers, such as polyvinyl acetate, which behave somewhat asplasticizers, are also often included. Other plastic polymers that maybe used include polyvinyl laureate, polyvinyl alcohol and polyvinylpyrrolidone.

Elastomers may include polyisobutylene, butyl rubber,(isobutylene-isoprene copolymer) and styrene butadiene rubber, as wellas natural latexes such as chicle. Elastomer solvents are often resinssuch as terpene resins. Plasticizers, sometimes called softeners, aretypically fats and oils, including tallow, hydrogenated and partiallyhydrogenated vegetable oils, and coca butter. Commonly employed waxesinclude paraffin, microcrystalline and natural waxes such as beeswax andcarnauba. Microcrystalline waxes, especially those with a high degree ofcrystallinity, may be considered bodying agents or textural modifiers.

According to the preferred embodiment of the present invention, theinsoluble gum base constitutes between about 5% to about 95% by weightof the gum. More preferably the insoluble gum base comprises between 10%and 50% by weight of the gum and most preferably about 20% to 35% byweight of the gum.

The gum base typically also includes a filler component. The fillercomponent may be calcium carbonate, magnesium carbonate, talc, dicalciumphosphate or the like. The filler may constitute between about 5% andabout 60% by weight of the gum base. Preferably the filler comprisesabout 5% to 50% by weight of the gum base.

Gum bases typically also contain softeners including glycerolmonostearate and glycerol triacetate. Gum bases may also containoptional ingredients such as antioxidants, colors, and emulsifiers. Thepresent invention contemplates employing any commercially acceptable gumbase.

The water-soluble portion of the chewing gum may further comprisesofteners, sweeteners, flavors, physiological cooling agents andcombinations thereof. The sweeteners often fulfill the role of bulkingagents in the gum. The bulking agents typically comprise about 5% toabout 95% of the gum composition.

Softeners are added to the chewing gum in order to optimize thechewability and mouth feel of the gum. Softeners, also known in the artas plasticizers or plasticizing agents, generally constitute betweenabout 0.5% to about 15% of the chewing gum. Softeners contemplated bythe present invention include glycerin, lecithin and combinationsthereof. Further, aqueous sweetener solutions such as those containingsorbitol, hydrogenated starch hydrolysate, corn syrup and combinationsthereof may be used as softeners and binding agents in gum.

As mentioned above, the cooling flavor compositions or coatedphysiological cooling agents of the present invention will most likelybe used in sugarless gum formulations. However, formulations containingsugar are also within the scope of the invention. Sugar sweetenersgenerally include saccharide-containing components commonly known in thechewing gum art which comprise, but are not limited to, sucrose,dextrose, maltose, dextrin, dried invert sugar, fructose, galactose,corn syrup solids and the like, alone or in any combination.

The cooling flavor compositions and coated physiological cooling agentsof the present invention can also be used in combination with sugarlesssweeteners. Generally sugarless sweeteners include components withsweetening characteristics but which are devoid of the commonly knownsugars and comprise, but are not limited to, sugar alcohols such assorbitol, hydrogenated isomaltulose, mannitol, xylitol, lactitol,erythintol, hydrogenated starch hydrolysate, maltitol and the like aloneor in any combination.

Depending on the particular sweetness release profile andshelf-stability needed, coated or uncoated high-intensity sweeteners maybe used in the chewing gum center or in the coating. High-intensitysweeteners, preferably aspartame, may be used at levels from about 0.01%to about 3.0%. Encapsulated aspartame is a high intensity sweetener withimproved stability and release characteristics, as compared to freeaspartame. Free aspartame can also be added, and a combination of somefree and encapsulated aspartame is preferred when aspartame is used.

Optional ingredients such as colors, emulsifiers and pharmaceuticalagents may also be added as separate components of the chewing gumcomposition, or added as part of the gum base.

Aqueous syrups, such as corn syrup and hydrogenated corn syrup may beused, particularly if their moisture content is reduced. This canpreferably be done by coevaporating the aqueous syrup with aplasticizer, such as glycerin or propylene glycol, to a moisture contentof less than 10%. Preferred compositions include hydrogenated starchhydrolysate solids and glycerin. Such syrups and their methods ofpreparation are discussed in detail in U.S. Pat. No. 4,671,967.

A preferred method of manufacturing chewing gum according to the presentinvention is by sequentially adding the various chewing gum ingredientsto any commercially available mixer known in the art. After theingredients have been thoroughly mixed, the gum is discharged from themixer and shaped into the desired form such as by rolling into sheetsand cutting into sticks, extruding into chunks, or casting into pellets.

Generally, the ingredients are mixed by first melting the gum base andadding it to the running mixer. the base may also be melted in the mixeritself. Color or emulsifiers may also be added at this time, along withsyrup and a portion of the bulking agent. Further portions of thebulking agent may then be added to the mixer. A flavoring agent istypically added with the final portion of the bulking agent. The coolingflavor composition of the present invention are preferably added as partof the flavor addition. The coated physiological cooling agents of thepresent invention are preferably added after the final portion ofbulking agent and flavor have been added. The entire mixing proceduretypically takes from five to fifteen minutes, but longer mixing timesmay sometime be required. Those skilled in the art will recognize thatmany variations of the above described procedures may be followed.

When the physiological cooling agent is used as part of a cooling flavorcomposition, using menthol and menthone, the cooling flavor compositionwill contain preferably about 40% to about 80%, and more preferablyabout 50% to about 70%, menthol, and about 15% to about 50%, and morepreferably about 20% to about 40%, menthone. In the preferred coolingflavor composition, the ratio of menthol to menthone is preferablybetween about 4:5 and about 16:3. The ratio of physiological coolingagents to the total of menthol and menthone is preferable between about3:97 and about 1:4. Typically this will mean about 3% to about 25%, andmore preferably about 4% to about 15% of the cooling composition will beone or more physiological cooling agents. The preferred physiologicalcooling agents are: menthyl succinate; N-2,3-trimethyl-2-isopropylbutanamide; menthyl lactate; 3-1-menthoxypropane-1,2-diol; N-substitutedp-menthane carboxamide; menthone glycerol ketals and mixture thereof.

If another flavor is used in the gum, or other oral composition, besidethe cooling flavor composition, the cooling flavor composition outlinedabove may be mixed with the other flavor. In addition, some componentsof the cooling flavor composition may be mixed with the other flavor,and some components added separately to the gum. However, It ispreferred that any other flavor and the cooling flavor composition bepremixed before being added to the gum.

Once formed, the chewing gum center can be coated. The coating isinitially present as a liquid syrup which contains from about 30% toabout 80% or 85% of the coating ingredients previously described herein,and from about 15% or 20% to about 70% of a solvent such as water. Ingeneral, the coating process is carried out in conventional panningequipment. Sugarless gum center tablets to be coated are placed into thepanning equipment to form a moving mass.

The material or syrup which will eventually form the coating is appliedor distributed over the gum center tablets. Flavors may be added before,during and after applying the syrup to the gum centers. Once the coatinghas dried to form a hard surface, additional syrup additions can be madeto produce a plurality of coatings or multiple layers of coating.

In the panning procedure, syrup is added to the gum center tablets at atemperature range of from about 100° F. to about 240° F. Preferably, thesyrup temperature is from about 140° F. to about 200° F. Mostpreferably, the syrup temperature should be kept constant throughout theprocess in order to prevent the polyol in the syrup from crystallizing.The syrup may be mixed with, sprayed upon, poured over, or added to thegum center tablets in any way known to those skilled in the art.

In another embodiment, a soft coating is formed by adding a powdercoating after a liquid coating. The powder coating may include naturalcarbohydrate gum hydrolysates, maltodextrin, gelatin, cellulosederivatives, starches, modified starches, sugars, sugar alcohols,natural carbohydrate gums and fillers like talc and calcium carbonate.

Each component of the coating on the gum center may be applied in asingle layer or in a plurality of layers. In general, a plurality oflayers is obtained by applying single coats, allowing the layers to dry,and then repeating the process. The amount of solids added by eachcoating step depends chiefly on the concentration of the coating syrup.Any number of coats may be applied to the gum center Tablet. Preferably,no more than about 75 coats are applied to the gum center. Morepreferably, less than about 60 coats are applied and most preferably,about 30 to about 60 coats are applied. In any event, the presentinvention contemplates applying an amount of syrup sufficient to yield acoated chewing gum product containing about 10% to about 65% coating.Preferably, the final product will contain from about 20% to about 50%coating.

Those skilled in the art will recognize that in order to obtain aplurality of coated layers, a plurality of premeasured aliquots ofcoating syrup may be applied to the gum center. It is contemplated,however, that the volume of aliquots of syrup applied to the gum centermay vary throughout the coating procedure.

Once a coating of syrup is applied to the gum center, the presentinvention contemplates drying the wet syrup in an inert medium. Apreferred drying medium comprises air. Preferably, forced drying aircontacts the wet syrup coating in a temperature range of from about 70°F. to about 110° F. More preferably, the drying air is in thetemperature range of from about 80° F. to about 100° F. The inventionalso contemplates that the drying air possess a relative humidity ofless than about 15 percent. Preferably, the relative humidity of thedrying air is less than about 8 percent.

The drying air may be passed over and admixed with the syrup coated gumcenters in any way commonly known in the art. Preferably, the drying airis blown over and around the syrup coated gum center at a flow rate, forlarge scale operations, of about 2800 cubic feet per minute. If lowerquantities of material are being processed, or if smaller equipment isused, lower flow rates would be used. If a flavor is applied after asyrup coating has been dried, the present invention contemplates dryingthe flavor with or without the use of a drying medium.

EXAMPLES

The following four ingredients can be mixed with flavors and used inchewing gum formulations. The percentage listed are percentages of thetotal of these four ingredients. However, the ingredients were not mixedtogether first, but were added individually to the flavor used in thegum. The four ingredients in combination are referred to herein ascooling blends A, B and C.

A B C Menthol 52.5 60.2 62.5 Menthone 25.8 30.6 31.2 Menthyl succinate14.5 6.1 4.2 Menthyl lactate 7.2 3.1 2.1

Examples 1 and 2

Cooling blend A may be mixed with a cherry flavor and used to make twocherry flavored sugarless gum formulas. Both products would have aslightly minty flavor with cherry. When a peppermint flavor is used inplace of the cooling blend in comparable formulas, the minty characteris too strong. The cooling blend gives a high quality cool cherry mintflavored product as formulated below:

TABLE 1 Example 1 Example 2 Sorbitol 49.51 51.44 Base 28.50 25.00Glycerin 12.00 12.00 Cherry Flavor 3.0848 2.8848 Cooling Blend A 0.11520.1152 Spray Dried Cherry Flavor 0.30 — Xylitol 1.50 4.50 Fumeric,Citric, and Adipic Acids 2.10 2.10 Encapsulated Sweeteners 1.36 1.36Salt Solution 0.75 — Color 0.28 0.30 Lecithin 0.50 0.30 TOTAL 100.00100.00

Examples 3, 4 and 5

Cooling blend B may be used in a sugarless wintergreen flavored chewinggum to give improved cooling without mint flavor according to thefollowing formulas:

TABLE 2 Example 3 Example 4 Example 5 Sorbitol 49.60 50.01 48.76 Base25.10 25.10 25.10 Glycerin 14.00 6.00 14.00 Maltitol 5.00 7.00 10.00Coevaporated Glycerin/Lycasin* 3.50 9.50 — Wintergreen Flavor 1.12961.1296 1.1296 Cooling Blend B 0.4704 0.4704 0.4704 EncapsulatedWintergreen Flavor 0.1625 0.1625 — Encapsulated Menthol 0.0875 0.0875 —Encapsulated Sweeteners 0.54 0.54 0.54 Salt Solution** 0.28 — — Color0.13 — — TOTAL 100.00 100.00 100.00 *Contains 25% glycerin, 67.5%Lycasin brand hydrogenated starch hydrolsate solids and 7.5% water.**Contains 10% NaCl and 90% water.

Examples 6 through 10

Cooling blend C was used in spearmint and peppermint flavored chewinggums of Examples 6 through 10 to give improved cooling with mint flavor.The increased cooling yielded products with less bitterness andharshness, and gave good minty tasting products. The following formulaswere made:

TABLE 3 Example 6 Example 7 Example 8 Example 9 Example 10 Sorbitol47.21 48.60 32.76 48.41 40.60 Base 25.00 25.00 37.35 25.00 30.00Glycerin 6.00 11.40 12.00 8.00 10.00 Coevaporated 9.50 7.67 — 9.50 3.50Glycerin/Lycasin* Maltitol^(A)/Mannitol^(B) 10.00^(A) 5.00^(A) 3.07^(B)5.00^(B) 7.00^(B) Spearmint Flavor 1.0908 1.0908 — — — Cooling Blend C0.2592 0.2592 0.7425 0.7425 0.40 Peppermint Flavor — — 1.5075 1.50751.60 Lecithin 0.30 0.30 0.40 0.30 0.30 Calcium Carbonate — — 9.66 — 5.00Encapsulated Menthol — 0.20 1.50 1.00 1.00 Encapsulated Sweetener 0.540.34 0.34 0.54 0.60 Salt Solution** 0.10 0.10 0.67 — — Color — 0.04 — —— TOTAL 100.00 100.00 100.00 100.00 100.00 *Contains 25% glycerin, 67.5%Lycasin brand hydrogenated starch hydrolsate solids and 7.5% water.**Contains 10% NaCl and 90% water.

Examples 11 through 17

The following formulations contain combinations of cooling agents thatmay give fast and slow release and may be synergistic to increasecooling when used in the same formulation:

TABLE 4 SUGARLESS CHEWING GUM Example 11 Example 12 Example 13 Example14 Base 33.10 28.00 30.00 28.00 Calcium — — 11.00 — Carbonate Sorbitol55.90 54.36 46.08 49.52 Glycerin 8.00 5.40 0.40 8.30 Liquid Sorbitol —6.00 6.20 2.00 Encapsulated 0.70 0.24 0.24 0.82 Sweetener Menthol 1.10 —0.26 0.30 Active 0.10 0.20 0.12 0.16 ML/TCA* Mannitol — 3.00 3.00 8.00Peppermint 1.10 2.00 — — Flavor Methyl — — 1.90 1.90 Salicylate FlavorLecithin — 0.80 0.80 1.00 Encapsulated — — — — Menthol/Flavor TOTAL100.00 100.00 100.00 100.00 *50/50 combination of ML and TCA

TABLE 5 SUGARLESS CHEWING GUM Example 15 Example 16 Example 17 Base29.00 31.60 33.60 Calcium Carbonate 15.00 11.00 13.00 Sorbitol 41.2644.48 47.73 Glycerin 10.00 0.80 0.75 Liquid Sorbitol — 7.20 —Encapsulated Sweetener 0.40 0.66 0.66 Menthol 0.90 0.30 0.30 ActiveML/MGK* 0.14 0.06 0.06 Mannitol — — — Peppermint Flavor 1.30 1.40 1.40Methyl Salicylate Flavor — — — Lecithin — 0.50 0.50 EncapsulatedMenthol/Flavor 2.00 2.00 2.00 TOTAL 100.00 100.00 100.00 *50/50combination of ML and MGK

N-substituted p-menthane carboxamides, for exampleN-ethyl-p-menthane-3-carboxamide (WS-3), when combined with menthoneketals such as menthone glycerol ketal, may produce synergistic coolingeffects in chewing gum. It is also possible to take advantage ofdiffering release rates of the two cooling agents to provide a fastcooling release and a long lasting cooling in the same product. Forexample, chewing gums may be prepared form the following formulas:

TABLE 6 Example 18 Example 19 Gum Base 25.00 30.00 Sugar 57.11 58.46Corn Syrup 15.00 9.00 Glycerin 2.00 1.50 Spearmint Oil 0.70 — PeppermintOil — 0.90 WS-3 0.08 0.06 Menthone Glycerol Ketal 0.11 0.08 TOTAL 100.00100.00

Additional cooling agents may also be added as in some of the followingexamples:

TABLE 7 Example Example Example Example Example Example 20 21 22 23 2425 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 49.0553.07 60.69 59.54 51.12 Hydrogenated Starch — — — 7.5 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 0.30 0.10 0.080.11 0.13 0.04 Menthane Glycerol Ketal 0.05 0.10 0.20 0.35 0.05 0.04WS-23 — 0.05 0.05 — — — Menthyl Lactate 0.30 — 0.20 — — 0.10 MenthylSuccinate — — — 0.20 0.08 0.10 100.00 100.00 100.00 100.00 100.00 100.00

Acyclic carboxamides, for example N-2,3-trimethyl-2-isopropyl butanamide(WS-23), may produce synergistic cooling effects when combined withmenthone ketals, such as menthone glycerol ketal, in chewing gum. It isalso possible to take advantage of differing release rates of the twocooling agents to provide a fast cooling release and a long lastingcooling in the same product. Also, reductions in bitterness may beachieved through optimization of the levels of these cooling agents. Forexample, chewing gums may be prepared from the following formulas:

TABLE 8 Example 26 Example 27 Gum Base 25.00% 30.00% Sugar 57.11% 58.46%Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70% —Peppermint Oil — 0.90% WS-23 0.08% 0.06% Menthone Glycerol Ketal 0.11%0.08% TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 9 Example Example Example Example Example Example 28 29 30 31 3233 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.9053.07 60.69 59.54 50.87 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-23 0.30 0.10 0.080.11 0.13 0.04 Manthone Glycerol Ketal 0.05 0.10 0.20 0.35 0.05 0.04WS-3 — 0.05 0.05 — — — Menthyl Lactate 0.30 — 0.20 — — 0.10 MenthylSuccinate — — — 0.20 0.08 0.10 Menthol — 0.15 — — — 0.25 100.00 100.00100.00 100.00 100.00 100.00

Acyclic carboxamides, for example N-2,3-trimethyl-2-isopropyl butanamide(WS-23), may produce synergistic cooling effects when combined withmenthol in chewing gum. It is also possible to take advantage ofdiffering release rates of the two cooling agents to provide a fastcooling release and a long lasting cooling in the same product. Also,reductions in bitterness may be achieved through optimization of thelevels of these cooling agents. For example, chewing gums may beprepared from the following formulas:

TABLE 10 Example 34 Example 35 Gum Base 25.00% 30.00% Sugar 56.76%58.29% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-23 0.04% 0.06% Menthol 0.50% 0.25% TOTAL100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 11 Example Example Example Example Example Example 36 37 38 39 4041 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 33.85 48.6053.12 60.69 59.54 50.46 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-23 0.30 0.10 0.080.11 0.13 0.04 Menthol 0.25 0.40 0.15 0.35 0.05 0.45 WS-3 — 0.05 0.05 —— — Menthyl Lactate 0.30 — 0.20 — — 0.10 Menthyl Succinate — — — 0.200.08 0.10 Menthone Glycerol Ketal — 0.15 — — — 0.25 100.00 100.00 100.00100.00 100.00 100.00

Menthyl succinate may produce synergistic cooling effects when combinedwith acyclic carboxamides, for example N-2,3-trimethyl-2-isopropylbutanamide (WS-23), in chewing gum. It is also possible to takeadvantage of differing release rates of the two cooling agents toprovide a fast cooling release and a long lasting cooling in the sameproduct. Also, reductions in bitterness may be achieved throughoptimization of the levels of these cooling agents. For example, chewinggums may be prepared from the following formulas:

TABLE 12 Example 42 Example 43 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-23 0.08% 0.06% Menthyl Succinate 0.11% 0.08%TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 13 Example Example Example Example Example Example 44 45 46 47 4849 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.8552.57 60.69 59.24 51.12 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 — — 0.08 0.16 — —Menthone Glycerol Ketal — — — — 0.05 0.04 WS-23 0.30 0.05 0.05 0.20 0.130.04 Menthyl Lactate 0.30 0.10 0.20 0.10 — 0.10 Menthyl Succinate 0.050.10 0.20 0.20 0.08 0.10 Menthol — 0.20 0.50 — 0.30 — 100.00 100.00100.00 100.00 100.00 100.00

Menthyl succinate may produce synergistic cooling effects when combinedwith menthone ketals, such menthone glycerol ketal, in chewing gum. Itis also possible to take advantage of differing release rates of the twocooling agents to provide a fast cooling release and a long lastingcooling in the same product. Also, reductions in bitterness may beachieved through optimization of the levels of these cooling agents. Forexample, chewing gums may be prepared from the following formulas:

TABLE 14 Example 50 Example 51 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% Menthyl Succinate 0.08% 0.06% Menthone GlycerolKetal 0.11% 0.08% TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 15 Example Example Example Example Example Example 52 53 54 55 5657 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.8552.57 60.69 59.24 51.12 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 — — — 0.05 0.08 —Menthone Glycerol Ketal 0.05 0.10 0.20 0.35 0.10 0.07 WS-23 — 0.05 0.05— — — Menthyl Lactate 0.30 — 0.20 — — 0.10 Menthyl Succinate 0.30 0.100.08 0.26 0.08 0.11 Menthol — 0.20 0.50 — 0.30 — 100.00 100.00 100.00100.00 100.00 100.00

Menthyl succinate may produce synergistic cooling effects when combinedwith menthyl lactate in chewing gum. It is also possible to takeadvantage of differing release rates of the two cooling agents toprovide a fast cooling release and a long lasting cooling in the sameproduct. Also, reductions in bitterness may be achieved throughoptimization of the levels of these cooling agents. For example, chewinggums may be prepared from the following formulas:

TABLE 16 Example 58 Example 59 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% Menthyl Lactate 0.08% 0.06% Menthyl Succinate0.11% 0.08% TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 17 Example Example Example Example Example Example 60 61 62 63 6465 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.8552.57 60.69 59.24 51.12 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 0.10 — 0.08 — —0.04 Menthone Glycerol Ketal 0.05 — — 0.11 0.05 0.04 WS-23 — 0.05 0.05 —— — Menthyl Lactate 0.30 0.10 0.25 0.35 0.13 0.10 Menthyl Succinate 0.200.10 0.15 0.20 0.08 0.10 Menthol — 0.20 0.50 — 0.30 — 100.00 100.00100.00 100.00 100.00 100.00

Menthyl succinate may produce synergistic cooling effects when combinedwith N-substituted p-menthane carboxamides, for exampleN-ethyl-p-menthane-3-carboxamide (WS-3), in chewing gum. It is alsopossible to take advantage of differing release rates of the two coolingagents to provide a fast cooling release and a long lasting cooling inthe same product. Also, reductions in bitterness may be achieved throughoptimization of the levels of these cooling agents. For example, chewinggums may be prepared from the following formulas:

TABLE 18 Example 66 Example 67 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-3 0.08% 0.06% Menthyl Succinate 0.11% 0.08%TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 19 Example Example Example Example Example Example 68 69 70 71 7273 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.8552.57 60.69 59.24 51.12 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 0.30 0.10 0.080.25 0.13 0.04 Menthone Glycerol Ketal — — — 0.05 0.05 0.04 WS-23 — 0.050.05 0.06 — — Menthyl Lactate 0.30 — 0.20 0.10 — 0.10 Menthyl Succinate0.05 0.10 0.20 0.20 0.08 0.10 Menthol — 0.20 0.50 — 0.30 — 100.00 100.00100.00 100.00 100.00 100.00

N-substituted p-menthane carboxamides, for exampleN-ethyl-p-menthane-3-carboxamide (WS-3), may produce synergistic coolingeffects when combined with acyclic carboxamides, for exampleN-2,3-trimethyl-2-isopropyl-butanamide (WS-23), in chewing gum. It isalso possible to take advantage of differing release rates of the twocooling agents to provide a fast cooling release and a long lastingcooling in the same product. Also, reductions in bitterness may beachieved through optimization of the levels of these cooling agents. Forexample, chewing gums may be prepared from the following formulas:

TABLE 20 Example 74 Example 75 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-3 0.08% 0.06% WS-23 0.11% 0.08% TOTAL 100.00100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 21 Example Example Example Example Example Example 76 77 78 79 8081 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.8552.57 60.69 59.24 51.08 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 0.30 0.10 0.080.21 0.13 0.04 Menthone Glycerol Ketal — — — 0.10 0.05 0.04 WS-23 0.050.15 0.25 0.10 0.04 0.10 Menthyl Lactate 0.30 — 0.20 0.05 — 0.07 MenthylSuccinate — — — 0.20 0.04 0.07 Menthol — 0.20 0.50 — 0.30 — 100.00100.00 100.00 100.00 100.00 100.00

Menthyl salicylate (wintergreen) may produce synergistic cooling effectswhen combined with acyclic carboxamides, for exampleN-2,3-trimethyl-2-isopropyl butanamide (WS-23), in chewing gum. It isalso possible to take advantage of differing release rates of the twocooling agents to provide a fast cooling release and a long lastingcooling in the same product. Also, reductions in bitterness may beachieved through optimization of the levels of these cooling agents. Forexample, chewing gums may be prepared from the following formulas.

TABLE 22 Example 82 Example 83 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-23 0.08% 0.06% Methyl salicylate 0.11% 0.08%TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 23 Example Example Example Example Example Example 84 85 86 87 8889 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.4051.77 60.74 59.24 51.02 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.70 0.80 1.20 0.70 0.90 1.00 Peppermint Oil1.00 0.40 — 0.20 — — Spearmint Oil 0.10 — 0.40 — — 0.30 WS-3 0.20 0.500.08 — — 0.04 Menthone Glycerol Ketal 0.05 0.10 0.20 0.35 0.05 0.04WS-23 0.30 0.10 0.05 0.11 0.13 0.08 Menthyl Lactate 0.30 — 0.20 — — 0.06Menthyl Succinate — — — 0.20 0.08 0.06 Menthol — 0.20 0.50 — 0.30 —100.00 100.00 100.00 100.00 100.00 100.00

Menthyl salicylate (wintergreen) may produce synergistic cooling effectswhen combined with N-substituted p-menthane carboxamides, for exampleN-ethyl-p-menthane-3-carboxamide (WS-3), in chewing gum. It is alsopossible to take advantage of differing release rates of the two coolingagents to provide a fast cooling release and a long lasting cooling inthe same product. Also, reductions in bitterness may be achieved throughoptimization of the levels of these cooling agents. For example, chewinggums may be prepared from the following formulas:

TABLE 24 Example 90 Example 91 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-3 0.08% 0.06% Methyl Salicylate 0.11% 0.08%TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 25 Example Example Example Example Example Example 92 93 94 95 9697 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.05 48.8551.77 59.75 58.94 51.02 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.85 0.80 1.20 0.70 0.90 1.00 Peppermint Oil1.00 0.40 — 1.20 0.20 — Spearmint Oil 0.15 — 0.40 — — 0.30 WS-3 0.250.20 0.08 0.20 0.13 0.04 Menthone Glycerol Ketal — — 0.10 0.25 0.05 0.04WS-23 0.10 0.05 0.05 — 0.10 — Menthyl Lactate 0.30 — 0.20 — — 0.10Menthyl Succinate — — 0.10 0.20 0.08 0.10 Menthol — 0.20 0.50 — 0.30 —100.00 100.00 100.00 100.00 100.00 100.00

The cooling agent 3-l-menthoxypropane-1,2-diol (TCA) from Takasago mayproduce synergistic cooling effects when combined with menthone ketals,such as menthone glycerol ketal, in chewing gum. It is also possible totake advantage of differing release rates of the two cooling agents toprovide a fast cooling release and a long lasting-cooling in the sameproduct. Also, reductions in bitterness may be achieved throughoptimization of the levels of these cooling agents. For example, chewinggums may be prepared from the following formulas:

TABLE 26 Example 98 Example 99 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% TCA 0.08% 0.06% Menthone Glycerol Ketal 0.11%0.08% TOTAL 100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 27 Example Example Example Example Example Example 100 101 102 103104 105 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.0548.90 53.07 60.69 59.54 50.87 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — TCA 0.30 0.10 0.080.11 0.13 0.04 Menthone Glycerol Ketal 0.05 0.10 0.20 0.35 0.05 0.04WS-3 — 0.05 0.05 — — — Menthyl Lactate 0.30 — 0.20 — — 0.10 MenthylSuccinate — — — 0.20 0.08 0.10 Menthol — 0.15 — — — 0.25 100.00 100.00100.00 100.00 100.00 100.00

The Takasago cooling agent (TCA) may produce synergistic cooling effectswhen combined with menthol in chewing gum. It is also possible to takeadvantage of differing release rates of the two cooling agents toprovide a fast cooling release and a long lasting cooling in the sameproduct. Also, reductions in bitterness may be achieved throughoptimization of the levels of these cooling agents. For example, chewinggums may be prepared from the following formulas:

TABLE 28 Example 106 Example 107 Gum Base 25.00% 30.00% Sugar 56.76%58.29% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% TCA 0.04% 0.06% Menthol 0.50% 0.25% TOTAL100.00 100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 29 Example Example Example Example Example Example 108 109 110 111112 113 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 33.8548.60 53.12 60.69 59.54 50.46 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — TCA 0.30 0.10 0.080.11 0.13 0.04 Menthol 0.25 0.40 0.15 0.35 0.05 0.45 WS-3 — 0.05 0.05 —— — Menthyl Lactate 0.30 — 0.20 — — 0.10 Menthyl Succinate — — — 0.200.08 0.10 Menthone Glycerol Ketal — 0.15 — — — 0.25 100.00 100.00 100.00100.00 100.00 100.00

The cooling agent 3-l-menthoxypropane-1,2-diol may produce synergisticcooling effects when combined with acyclic carboxamides, for exampleN-2,3-trimethyl-2-isopropyl butanamide (WS-23), in chewing gum. It isalso possible to take advantage of differing release rates of the twocooling agents to provide a fast cooling release and a long lastingcooling in the same product. Also, reductions in bitterness may beachieved through optimization of the levels of these cooling agents. Forexample, chewing gums may be prepared from the following formulas:

TABLE 30 Example 114 Example 115 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-23 0.08% 0.06% TCA 0.11% 0.08% TOTAL 100.00100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 31 Example Example Example Example Example Example 116 117 118 119120 121 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.0548.85 52.57 60.69 59.24 51.12 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 — — 0.08 0.16 — —Menthone Glycerol Ketal — — — — 0.05 0.04 WS-23 0.30 0.05 0.05 0.20 0.130.04 Menthyl Lactate 0.30 0.10 0.20 0.10 — 0.10 TCA 0.05 0.10 0.20 0.200.08 0.10 Menthol — 0.20 0.50 — 0.30 — 100.00 100.00 100.00 100.00100.00 100.00

The cooling agent 3-l-menthoxypropane-1,2-diol may produce synergisticcooling effects when combined with N-substituted p-menthanecarboxamides, for example N-ethyl-p-menthane-3-carboxamide (WS-3), inchewing gum. It is also possible to take advantage of differing releaserates of the two cooling agents to provide a fast cooling release and along lasting cooling in the same product. Also, reductions in bitternessmay be achieved through optimization of the levels of these coolingagents. For example, chewing gums may be prepared from the followingformulas:

TABLE 32 Example 122 Example 123 Gum Base 25.00% 30.00% Sugar 57.11%58.46% Corn Syrup 15.00% 9.00% Glycerin 2.00% 1.50% Spearmint Oil 0.70%— Peppermint Oil — 0.90% WS-3 0.08% 0.06% TCA 0.11% 0.08% TOTAL 100.00100.00Additional cooling agents may also be added as in some of the followingexamples:

TABLE 33 Example Example Example Example Example Example 124 125 126 127128 129 Gum Base 48.00 35.00 30.00 25.00 22.00 30.00 Sorbitol 34.0548.85 52.57 60.69 59.24 51.12 Hydrogenated Starch — — — 7.50 14.00 10.00Hydrolysate Syrup 70% Sorbitol Solution 10.00 8.00 — — — — Glycerin 5.006.00 15.00 5.00 3.00 7.00 Encapsulated Aspartame 0.30 0.50 0.60 0.200.30 0.40 Methyl Salicylate 0.50 — — — 0.70 — Peppermint Oil 1.30 0.40 —0.95 0.20 1.20 Spearmint Oil 0.20 0.80 0.80 — — — WS-3 0.30 0.10 0.080.25 0.13 0.04 Menthone Glycerol Ketal — — — 0.05 0.05 0.04 WS-23 — 0.050.05 0.06 — — Menthyl Lactate 0.30 — 0.20 0.10 — 0.10 TCA 0.05 0.10 0.200.20 0.08 0.10 Menthol — 0.20 0.50 — 0.30 — 100.00 100.00 100.00 100.00100.00 100.00

The above tables show formulations in a peppermint flavored, spearmintflavored or wintergreen flavored chewing gum. Other gum products can bemade with other flavors as well. Menthol and/or physiological coolingagents may enhance these various types of flavors, such asmenthol-eucalyptus, spearmint-menthol, cinnamon-menthol, and even fruitymint-menthol.

The formulations for various flavored gum formulas are found in tables34 and 35. Again, the cooling agents may (Examples 130-136) or may notbe encapsulated, depending on whether a modified release is desired.

TABLE 34 VARIOUS-FLAVORED SUGARLESS GUM Example Example Example Example130 131 132 133 Gum Base 30.00 30.00 30.00 30.00 Calcium Carbonate 5.005.00 5.00 5.00 Sorbitol 54.60 53.68 53.80 55.05 Glycerin 8.00 8.00 8.007.00 Encapsulated Sweetener 0.50 0.50 0.50 0.50 Flavor 1.00^(A) 1.50^(B)1.40^(B) 1.60^(C) Menthol 0.20 0.12 0.30 0.20 Active ML/PMC^(D) 0.100.20 0.10 0.05 Lecithin 0.60 0.60 0.60 0.60 Encapsulated Menthol — 0.400.30 — TOTAL 100.00 100.00 100.00 100.00 ^(A)Spearmint Flavor^(B)Menthol-Eucalyptus Flavor ^(C)Cinnamon-Menthol Flavor ^(D)50/50blend of ML and PMC compounds

TABLE 35 VARIOUS-FLAVORED SUGARLESS GUM Example 134 Example 135 Example136 Gum Base 30.00 30.00 30.00 Calcium Carbonate 5.00 5.00 5.00 Sorbitol53.90 52.30 52.30 Glycerin 8.00 10.00 10.00 Encapsulated Sweetener 0.500.60 0.60 Flavor 1.60^(C) 1.20^(D) 1.20^(D) Menthol 0.20 0.20 0.10Active ML/Acyclic 0.20 0.10 0.20 Carboxamide (AC)* Lecithin 0.60 0.600.60 Encapsulated Menthol — — — TOTAL 100.00 100.00 100.00 *50/50 blendof ML and acyclic carboxamide (AC) ^(C)Cinnamon-Menthol Flavor^(D)Fruity-Mint Menthol Flavor

The combination of physiological cooling agents may be used in a widevariety of sugarless and sugar chewing gum formulations. The coolingagents may be encapsulated or entrapped in a wide variety of controlledrelease techniques as previously discussed. Gum formulations in whichthese materials may be used are given in tables 36-42. These formulasmay also be made with non-encapsulated physiological cooling agents.Examples of the techniques and resulting controlled releasephysiological cooling agents that may be used in these formulations arediscussed in the examples following the tables.

TABLE 36 Regular-Tack Sugarless Gum Example Example Example ExampleExample 137 138 139 140 141 Sorbitol 50.00 50.00 50.00 50.00 50.00 GumBase 24.70 24.70 24.70 24.70 24.70 Lecithin 0.20 0.20 0.18 0.18 0.18Glycerin 2.00 2.00 2.00 5.00 8.00 Lycasin 14.40 12.00 12.00 9.00 6.00Mannitol 7.10 9.50 9.48 9.53 9.53 Peppermint 1.40 1.40 1.44 1.44 1.44Flavor Active Level 0.20 0.20 0.20 0.15 0.15 of Cooling Agents TOTAL100.00 100.00 100.00 100.00 100.00

TABLE 37 Regular-Tack Sugarless Gum Example Example Example ExampleExample 142 143 144 145 146 Sorbitol 49.35 49.35 49.35 49.35 49.35 GumBase 25.50 25.50 25.50 25.50 25.50 Lecithin 0.20 0.20 0.20 0.20 0.20Glycerin 8.50 8.50 8.50 8.60 8.50 Liquid 6.80 6.80 6.80 6.80 6.90Sorbitol Mannitol 8.00 8.00 8.00 8.00 8.00 Active Level 0.20 0.20 0.200.10 0.10 of Cooling Agents Peppermint 1.45 1.45 1.45 1.45 1.45 FlavorTOTAL 100.00 100.00 100.00 100.00 100.00

TABLE 38 Sugarless Pellet Gums for Coating Example Example ExampleExample Example 147 148 149 150 151 Sorbitol 51.16 43.87 45.92 43.8146.33 Gum Base 31.01 33.00 32.71 33.03 30.97 Glycerin 6.14 8.00 7.507.98 7.82 Aspartame 0.06 — 0.10 — 0.08 Active Level 0.42 0.23 0.35 0.250.34 of Cooling Agents Calcium 10.01 13.00 12.16 12.93 13.04 CarbonatePeppermint — 1.20 0.17 — 1.01 Flavor Menthol — 0.50 — — 0.21 FruitFlavor — — — 1.50 — Lemon — — — .50 — Flavor Encapsulated — 0.20 — —0.20 Menthol Spearmint 1.20 — 1.09 — — Flavor TOTAL 100.00 100.00 100.00100.00 100.00

TABLE 39 Sugarless Bubble Gums Example Example Example Example 152 153154 155 Sorbitol 56.65 56.09 50.42 48.63 Gum Base 24.00 24.59 28.0030.10 Lecithin 1.00 0.91 0.89 0.86 Fruit Flavor 1.20 1.41 — — GrapeFlavor — — 1.71 — Strawberry Flavor — — — 1.41 Evaporated — 6.79 9.6110.41 Lycasin/Glycerin* Glycerin 17.00 10.00 9.00 8.21 Free Aspartame0.04 — 0.06 0.17 Active Level of 0.11 0.21 0.31 0.21 Cooling AgentsTOTAL 100.00 100.00 100.00 100.00 *Contains 25% glycerin, 67.5% Lycasinbrand hydrogenated starch hydrolsate solids and 7.5% water.

TABLE 40 Sugar Gums Example Example Example Example Example 156 157 158159 160 Sugar 58.29 59.26 62.49 59.97 56.61 Gum Base 22.38 20.60 20.0823.17 26.80 Corn Syrup 17.20 18.50 15.40 14.70 13.88 Glycerin 1.09 0.831.00 1.00 1.30 Active Level 0.10 0.20 0.15 0.25 0.20 of Cooling AgentsLecithin 0.05 0.03 0.02 — — Peppermint 0.89 0.58 0.86 0.91 1.21 FlavorTOTAL 100.00 100.00 100.00 100.00 100.00

TABLE 41 Sugar Gums Example Example Example Example Example 161 162 163164 165 Sugar 54.30 45.30 49.30 40.30 45.30 Gum Base 19.20 19.20 19.2019.20 19.20 Glycerin 1.40 1.40 1.40 1.40 1.40 Corn Syrup 19.00 23.0019.00 19.00 23.00 Dextrose — 5.00 — — — Lactose 5.00 — — — — Fructose —5.00 — — — Invert Sugar — — 10.00 — — Maltose — — — 10.00 — Palatinose —— — — 10.00 Spearmint 0.90 0.90 0.90 9.90 0.90 Flavor Active Level 0.200.20 0.20 0.20 0.20 of Cooling Agents TOTAL 100.00 100.00 100.00 100.00100.00

TABLE 42 Sugarless Gums Example Example Example Example Example ExampleExample Example 166 167 168 169 170 171 172 173 Gum Base 25.50 25.5025.50 25.50 25.50 25.50 25.50 25.50 Sorbitol 53.80 46.80 41.80 41.8041.80 41.80 36.80 37.80 Sorbitol Liquid/ 17.00 14.00 6.00 — 5.00 — —11.00^(A) Lycasin Mannitol — 10.00 8.00 8.00 8.00 8.00 8.00 8.00Maltitol — — — 5.00 — — 5.00 — Xylitol — — 15.00 10.00 — — 5.00 10.00Lactitol — — — — 10.00 — — — Hydrogenated — — — — — 15.00 10.00 —Isomaltulose Glycerin 2.00 2.00 2.00 8.00 8.00 8.00 8.00 6.00 Flavor1.50 1.50 1.50 1.50 1.50 1.50 1.50 1.50 Active Level of 0.20 0.20 0.200.20 0.20 0.20 0.20 0.20 Cooling Agents TOTAL 100.00 100.00 100.00100.00 100.00 100.00 100.00 100.00 ^(A)Lycasin brand hydrogenated starchhydrolsate syrup; all others use 70% sorbitol liquid.

Encapsulated cooling agents may be made by the Examples 174-226 thatfollow and added to any of the formulas given in tables 36 through 42.Encapsulations with water soluble polymers such as HPMC or maltodextrinswill give a fast release of cooling agent. Encapsulations with shellac,Zein or PVAC will give a slow release.

Example 174

This example contains a cooling agent composition which has 25% menthylsuccinate and 75% PMC entrapped with polyvinyl-acetate.

Example 175

This example contains a cooling agent composition containing 50% menthylsuccinate and 50% PMC agglomerated with hydroxypropylmethyl cellulose.

Example 176

This example contains a cooling agent composition which has 75% menthylsuccinate and 25% PMC coated with Zein.

Example 177

This example contains a cooling agent composition which has 25% menthyllactate and 75% MGK absorbed onto silica.

Example 178

This example contains a cooling agent composition which has 50% menthylsuccinate and 50% MGK coated with shellac.

Example 179

This example contains a cooling agent composition which has 25% menthylsuccinate and 75% 3-l-menthoxypropane-1,2-diol (TCA) extruded withpolyvinyl acetate.

Example 180

This example contains a cooling agent composition which has 50% menthylsuccinate and 50% 3-l-menthoxypropane-1,2-diol (TCA) coated withshellac.

Example 181

This example contains a cooling agent composition which has 75% menthylsuccinate and 25% 3-l-menthoxypropane-1,2-diol (TCA) coated with Zein.

Example 182

This example contains a cooling agent composition which has 25% menthylsuccinate and 75% MGK extruded with polyvinyl acetate.

Example 183

This example contains a cooling agent composition which has 50% menthylsuccinate and 50% MGK coated with Zein.

Example 184

This example contains a cooling agent composition which has 75% menthylsuccinate and 25% MGK agglomerated with hydroxypropylmethyl cellulose.

Example 185

This example contains a cooling agent composition which has 25% menthylsuccinate and 75% acyclic carboxamide (AC) coated with Zein.

Example 186

This example contains a cooling agent composition which has 50% menthylsuccinate and 50% acyclic carboxamide (AC) coated withhydroxypropylmethyl cellulose.

Example 187

This example contains a cooling agent composition which has 75% menthylsuccinate and 25% acyclic carboxamide (AC) absorbed onto silica.

Example 188

This example contains a cooling agent composition which has 25% ML and75% 3-l-menthoxypropane-1,2-diol (TCA) agglomerated with gelatin.

Example 189

This example contains a cooling agent composition which has 50% ML and50% 3-l-menthoxypropane-1,2-diol (TCA) absorbed onto silica.

Example 190

This example contains a cooling agent composition which has 75% ML and25% 3-l-menthoxypropane-1,2-diol (TCA) coated with shellac.

Example 191

This example contains a cooling agent composition which has 50% ML and50% acyclic carboxamide (AC) which is agglomerated with Zein.

Example 192

This example contains a cooling agent composition which has 25% ML and75% acyclic carboxamide (AC) which is agglomerated withhydroxypropylmethyl cellulose.

Example 193

This example contains a cooling agent composition which has 75% ML and25% acyclic carboxamide (AC) coated with shellac.

Example 194

This example contains a cooling agent composition which has 50% menthyllactate and 50% p-menthane carboxamide (PMC) coated with maltodextrin.

Example 195

This example contains a cooling agent composition which has 25%3-l-menthoxypropane-1,2-diol and 75% acyclic carboxamide (AC) extrudedwith polyvinyl acetate.

Example 196

This example contains a cooling agent composition which has 50%3-1-menthoxypropane-1,2-diol and 50% p-menthane carboxamide (PMC)agglomerated with Zein.

Example 197

An 80% shellac, 20% active cooling agent powder mixture is obtained byspray drying an alcohol/shellac/menthyl succinate and menthyl lactatesolution.

Example 198

A 50% shellac, 50% active cooling agent powder mixture is obtained byspray drying an appropriate ratio of alcohol/shellac/menthyl succinateand menthyl lactate solution.

Example 199

A 70% Zein, 30% active cooling agent powder mixture is obtained by spraydrying an alcohol/shellac/menthyl succinate and menthyl lactatesolution.

Example 200

A shellac/silica/active cooling agent powder mixture is obtained byfluid-bed coating menthyl lactate and MGK absorbed on silica with analcohol/shellac solution at 20% solids.

Example 201

A shellac/silica/active cooling agent powder mixture is obtained byfluid-bed coating menthyl succinate and 3-l-menthoxypropane-1,2-diol(TCA) absorbed on silica with an alcohol/shellac solution at 20% solids.

Example 202

A Zein/silica/active cooling agent mixture is obtained by fluid-bedcoating menthyl succinate and menthyl lactate absorbed on silica with analcohol/Zein solution at 25% solids.

Example 203

An 85% wax, 15% active PMC and AC powder mixture is obtained by spraychilling a mixture of molten wax and cooling agent.

Example 204

A 70% wax, 30% active PMC and AC powder mixture is obtained by spraychilling a mixture of molten wax and cooling agent.

Example 205

A 70% Zein, 30% active menthyl succinate and p-menthane carboxamide(PMC) powder mixture is obtained by spray drying an aqueous mixture ofcooling agent and Zein dispersed in an aqueous, high-pH (pH=11.6-12.0)media at 15% solids.

Example 206

A Zein/active menthyl succinate and p-menthane carboxamide (PMC) powdermixture is obtained by fluid-bed coating cooling agent with an aqueous,high-pH (pH=11.6-12.0) Zein dispersion of 15% solids.

Example 207

A 20% Zein, 20% shellac, 60% active menthyl succinate and AC powdermixture is obtained by spray drying an alcohol/shellac/cooling agentmixture and then fluid-bed coating the spray dried product for a secondcoating of alcohol and Zein.

Examples 197-207 would all give nearly complete encapsulation and woulddelay the release of the cooling agents when used in gum formulations intables 36 through 42. The higher levels of coating would give a longerdelayed release of the cooling agents than the lower levels of coating.

Other polymers that are more water soluble and used in coating wouldhave less of an effect of delaying the release of the cooling agents.

Example 208

An 80% gelatin, 20% active PMC and TCA compounds powder mixture isobtained by spray drying a gelatin/TCA and PMC compounds emulsion.

Example 209

A 50% hydroxypropylmethyl cellulose (HPMC), 50% active menthyl succinateand PMC compounds powder mixture is obtained by fluid-bed coatingmenthyl succinate and PMC compounds with an aqueous solution of HPMC at10% solids.

Example 210

A 30% ethyl cellulose, 70% active menthyl succinate and PMC compoundspowder mixture is obtained by fluid-bed coating menthyl succinate andPMC compounds with an aqueous solution of ethyl cellulose at 10% solids.

Example 211

A 50% maltodextrin, 50% active TCA and AC compounds powder mixture isobtained by spray drying an aqueous emulsion of TCA and AC compounds andmaltodextrin at 40% solids.

Example 212

A 50% gum arabic, 50% active TCA and AC compounds powder mixture isobtained by fluid-bed coating TCA and AC compounds absorbed on silica,then with an aqueous solution of gum arabic at 40% solids.

The coated TCA and PMC compounds from Example 208, and the coatedmenthyl succinate and PMC compounds of Examples 209 and 210, when usedin the chewing gum formula in tables 36 through 42, would give amoderately fast release of cooling agents. The products coated withmaltodextrin and gum arabic in Examples 211 and 212, when used in thegum formula in tables 36 through 42, would give a fast release of thecooling agents.

Cooling agents could also be used in gum after being agglomerated togive modified release of these cooling agents.

Example 213

A 15% hydroxypropylmethyl cellulose (HPMC), 85% active TCA and PMCcompounds powder mixture can be prepared by agglomerating TCA and PMCcompounds and HPMC blended together, with water being added, and theresulting product being dried and ground.

Example 214

A 15% gelatin, 85% active TCA and PMC compounds powder mixture can bemade by agglomerating TCA and PMC compounds and gelatin blendedtogether, with water being added, and the resulting product being driedand ground.

Example 215

A 10% Zein, 90% active TCA and AC compounds powder mixture can be madeby agglomerating TCA and AC compounds with an aqueous solutioncontaining Zein, and drying and grinding the resulting product.

Example 216

A 15% shellac, 85% active TCA and AC compounds powder mixture can bemade by agglomerating TCA and AC compounds with an alcohol solutioncontaining 25% shellac, and drying and grinding the resulting product.

Examples of multiple step treatments are here described:

Example 217

Menthyl succinate and TCA are spray dried with maltodextrin at 30%solids to prepare a powder. This powder is then agglomerated with ahydroxypropylmethyl cellulose (HPMC) in a ratio of 85/15 powder/HPMC,wetted with water and dried. After grinding the resulting powder willcontain about 68% active cooling agent, 17% maltodextrin and 15% HPMC.

Example 218

Menthyl succinate and ML is agglomerated with HPMC in a ratio of 85/15cooling agent/HPMC. After drying and grinding, the resulting powder isfluid-bed coated with an alcohol shellac solution at about 25% solids togive a final product containing about 60% active cooling agent, 10%HPMC, and about 30% shellac.

Example 219

Menthyl succinate and ML is agglomerated with HPMC in a ratio of 85/15cooling agent/HPMC. After drying and grinding, the resulting powder isagglomerated with a 15% solids, high-pH, aqueous solution of Zein togive a final product containing about 60% active cooling agent, 10%HPMC, and 30% Zein.

Example 220

Menthyl lactate and TCA is spray dried with a 25% emulsion of gelatin.The spray dried product is then agglomerated with a 15% solids, high-pH,aqueous solution of Zein. The final product will contain about 50%active cooling agent, 20% gelatin, and 30% Zein.

Example 221

Menthyl succinate and AC is agglomerated with molten wax in a ratio of85/15 cooling agent/wax. When the mixture cools and is ground, it isfluid-bed coated with a 10% Zein solution, giving a final productcontaining 60% active cooling agent, 10% wax, and 30% Zein.

Example 222

A mixture of MGK and TCA is sprayed onto a precipitated silica. Themixture is dried and ground. The final product is about 50% activecooling agent.

Example 223

A mixture of MGK and TCA is sprayed onto a pharmasorb clay. The mixtureis dried and ground and gives a final product of about 80% clay and 20%active cooling agent.

Example 224

A mixture of MGK and TCA is sprayed onto a microcrystalline cellulosepowder. The mixture is dried and ground and gives a product that isabout 70% microcrystalline cellulose and 30% active cooling agent.

Example 225

A mixture of MGK and TCA is sprayed onto a high absorption starch. Themixture is dried and ground and gives a product that is about 80% starchand 20% active cooling agent.

Example 226

A mixture of MGK and TCA is sprayed onto a calcium carbonate powder. Themixture is dried and ground and gives a product of about 90% calciumcarbonate and 10% active cooling agent.

Many of the examples listed are single step processes. However, moredelayed release of the cooling agents may be obtained by combining thevarious processes of encapsulation, agglomeration, absorption, andentrapment. Any of the above preparations can be further treated influid-bed coating, spray chilling or coacervation processes toencapsulate the product, and can be agglomerated with various materialsand procedures in a variety of multiple step processes.

As disclosed in many of the patents, physiological cooling agents may beadded to chewing gum formulations. These chewing gums may be used ascenters or cores for the chewing gum that are coated. TABLE 43illustrates sugared chewing gum formulations that are used as centersfor sugar-coated chewing gums having a coating comprising aphysiological cooling agent.

TABLE 43 SUGARED CHEWING GUM CENTERS Example 227 Example 228 Example 229Gum Base 28.0% 30.0% 30.0% Sugar 52.9% 50.7% 46.6% Corn Syrup 18.0%18.0% 12.0% Glycerin  0.5%  0.5%  0.5% Spearmint Flavor  0.6% — —Peppermint Flavor —  0.8%  0.9% Dextrose Monohydrate — — 10.0%

The chewing gum formed in TABLE 43 is sheeted in pellets that are squareor rectangular pillow shaped and coated with the sugar-based coatingformulations in which the cooling agent and menthol are dissolved in theflavor when mixed into the coating syrup in TABLE 44.

TABLE 44 COATING FOR SUGARED CHEWING GUM CENTERS Example 230 Example 231Example 232 Sugar 96.56 96.06 95.71 Modified Starch 3.0 3.0 3.0Spearmint Flavor 0.3 — — Peppermint Flavor 0.6 0.8 Menthol — 0.2 0.3Carnauba Wax 0.04 0.04 0.04 Cooling Agent* 0.1 0.1 0.15 *Any of thecooling agents listed such as PMC, AC, ML, MS, MGK, TCA or combinationsmay be used.

In Example 230, the physiological cooling agent gives a clean, coolSpearmint flavor that could not be obtained with menthol. Examples 231and 232 would normally require higher levels of menthol, andconsequently would contain harsh notes. The addition of thephysiological cooling agents to Examples 231 and 232 result in strong,clean, cool minty tasting products.

As stated previously, non-sugar or sugarless coatings generally willhave less sweetness, thus causing more harsh notes when mint flavorand/or menthol are added to the coating. Use of the physiologicalcooling agents is especially useful in sugarless coating. Polyols suchas sorbitol, xylitol, maltitol, lactitol and hydrogenated isomaltulosecan be used to coat pellet sugarless gum. Examples of sugarless gumcenter or core formulations are found in tables 45 and 46.

TABLE 45 SUGARLESS GUM CENTERS Example Example Example Example 233 234235 236 Base 33.1 30.0 30.0 33.0 Calcium Carbonate 15.0 11.0 11.0 13.0Sorbitol 40.94 46.36 46.08 49.52 Glycerin 8.0 0.4 0.4 0.4 LiquidSorbitol — 6.2 6.2 — Encap. Sweetener 0.7 0.24 0.24 0.82 WintergreenFlavor 1.1 — — — Menthol 1.1 — 0.26 0.3 Cooling Agent* 0.06 — 0.12 0.06Mannitol — 3.0 3.0 — Peppermint Flavor — 2.0 1.9 1.9 Lecithin — 0.8 0.81.0 Encap Menthol — — — — *Any of the cooling agents listed such as PMC,AC, ML, MS, MGK, TCA or combinations may be used.

TABLE 46 SUGARLESS GUM CENTERS Example Example Example 237 238 239 Base32.0 31.6 33.6 Calcium Carbonate 15.0 11.0 13.0 Sorbitol 41.26 45.9849.23 Glycerin 7.0 0.8 0.75 Liquid Sorbitol — 7.2 — Encap. Sweetener0.40 0.66 0.66 Wintergreen Flavor — — — Menthol 0.9 0.3 0.3 CoolingAgents* 0.14 0.06 0.06 Mannitol — — — Peppermint Flavor 1.3 1.9 1.9Lecithin — 0.5 0.5 Encap Menthol 2.0 — — *Any of the cooling agentslisted such as PMC, AC, ML, MS, MGK, TCA or combinations may be used.

The centers in tables 45 and 46 are coated with coating formulationsthat comprise xylitol, maltitol, lactitol, hydrogenated isomaltulose orsorbitol; various flavors; optionally menthol; and the physiologicalcooling agents. Examples of sugarless coated chewing gums are found intables 47 and 48.

TABLE 47 SUGARLESS COATED CHEWING GUMS Ex. 240 Ex. 241 Ex. 242 Ex. 243Ex. 244 Center Ex. 233 Ex. 234 Ex. 234 Ex. 235 Ex. 236 Xylitol 88.8388.83 — — — Gum Arabic 8.8 8.8 2.8 2.8 3.1 Titanium Dioxide 0.9 0.9 0.90.9 1.3 Hydrogenated — — 95.0 94.84 93.66 isomaltulose Maltitol — — — —— Wintergreen Flavor 0.9 — — — — Peppermint Flavor — 0.9 0.7 0.7 0.75Menthol 0.4 0.4 0.3 0.5 0.75 Carnauba Wax 0.1 0.1 0.1 0.1 0.1 CoolingAgent* 0.07 0.07 0.1 0.06 0.14 Sweetener — — 0.1 0.1 0.2 *Cooling agentused in the examples may contain ML, MS, MGK, AC, PMC, TCA orcombinations

TABLE 48 SUGARLESS COATED CHEWING GUMS Ex. 245 Ex. 246 Ex. 247 Ex. 248Center Ex. 236 Ex. 237 Ex. 238 Ex. 239 Xylitol — — — — Gum Arabic 3.13.1 3.1 3.1 Titanium Dioxide 1.3 1.3 1.3 1.3 Hydrogenated Isomaltulose —— 93.59 93.56 Maltitol 93.66 93.33 — — Wintergreen Flavor — — — —Peppermint Flavor 0.75 1.0 0.9 0.9 Menthol 0.75 1.0 0.3 0.3 Carnauba Wax0.1 0.1 0.1 0.1 Cooling Agent* 0.14 0.02 0.11 0.14 Sweetener 0.2 0.150.6 0.6 *Cooling agent used in the examples may contain ML, MS, MGK, AC,PMC, TCA or combinations

In the examples of tables 47 and 48, menthol is dissolved into theflavor along with the physiological cooling agent. Half of this mixtureis applied at each of coats 8 and 14. After the coating is completed andallowed to stand overnight, the pellets are polished with carnauba wax.In the case of hydrogenated isomaltulose and maltitol, gum arabic may beused as a precoat with hydrogenated isomaltulose or maltitol, or dustedwith powdered hydrogenated isomaltulose or maltitol then coated with ahydrogenated isomaltulose or maltitol solution.

Other coated gum products can be made with other flavors as well.Menthol and/or physiological cooling agents may enhance these varioustypes of flavors such as menthol-eucalyptus, spearmint-menthol,cinnamon-menthol, and even fruity mint-menthol. The formulations forvarious flavored centers are found in tables 49 and 50.

TABLE 49 VARIOUS-FLAVORED CENTERS Ex. 249 Ex. 250 Ex. 251 Ex. 252 Base30.0 30.0 30.0 30.0 Calcium Carbonate 11.0 11.0 11.0 11.0 Sorbitol 51.650.6 50.8 52.05 Glycerin 5.0 5.0 5.0 4.0 Encap. Sweetener 0.5 0.5 0.50.5 Flavor 1.0^(A) 1.5^(B) 1.4^(B) 1.6^(C) Menthol 0.2 0.4 0.3 0.2Cooling agent* 0.1 — 0.1 0.05 Lecithin 0.6 0.6 0.6 0.6 Encap. Menthol —0.4 0.3 — ^(A)Spearmint Flavor ^(B)Menthol-Eucalyptus Flavor^(C)Cinnamon-Menthol Flavor *Cooling agent used in the examples maycontain ML, MS, MGK, AC, PMC, TCA or combinations

TABLE 50 VARIOUS-FLAVORED CENTERS Ex. 253 Ex. 254 Ex. 255 Base 30.0 30.030.0 Calcium Carbonate 11.0 11.0 11.0 Sorbitol 51.9 49.3 49.3 Glycerin4.0 7.0 7.0 Encap. Sweetener 0.5 0.6 0.6 Flavor 1.6^(C) 1.2^(D) 1.2^(D)Menthol 0.2 0.2 0.1 Cooling Agent* 0.2 0.1 0.2 Lecithin 0.6 0.6 0.6Encap. Menthol — — — ^(C)Cinnamon-Menthol Flavor ^(D)Fruity-mint MentholFlavor *Cooling agent used in the examples may contain ML, MS, MGK, AC,PMC, TCA or combinations

The various-flavored center formulas may be coated with polyols such asxylitol, maltitol, lactitol, hydrogenated isomaltulose or sorbitol andhave a physiological cooling agent added to the coating. Examples ofcoated chewing gum having various flavors are found in tables 51 and 52.

TABLE 51 VARIOUS-FLAVORED COATED CHEWING GUMS Ex. 256 Ex. 257 Ex. 258Ex. 259 Center Ex. 249 Ex. 250 Ex. 251 Ex. 252 Xylitol 89.7 89.1 — 89.2Gum Arabic 8.8 8.8 2.8 8.8 Titanium Dioxide 0.8 0.8 0.8 0.8 Hydrogenatedisomaltulose — — 95.0 — Maltitol — — — — Flavor 0.4^(A) 0.6^(B) 0.6^(B)0.8^(C) Menthol 0.1 0.4 0.3 0.2 Carnauba Wax 0.1 0.1 0.1 0.1 CoolingAgent* 0.1 0.2 0.2 0.1 Sweeteners — — 0.2 — ^(A)Spearmint Flavor^(B)Menthol-Eucalyptus Flavor ^(C)Cinnamon-Menthol Flavor *Cooling agentused in the examples may contain ML, MS, MGK, AC, PMC, TCA orcombinations

TABLE 52 VARIOUS-FLAVORED COATED CHEWING GUMS Ex. 260 Ex. 261 Ex. 262Center Ex. 253 Ex. 254 Ex. 255 Xylitol — 89.7 — Gum Arabic 2.8 8.8 2.8Titanium Dioxide 0.8 0.8 0.8 Hydrogenated isomaltulose 94.9 — — Maltitol— — 95.6 Flavor 0.8^(C) 0.3^(D) 0.3^(D) Menthol 0.2 0.1 0.1 Carnauba Wax0.1 0.1 0.1 Cooling Agent* 0.2 0.2 0.1 Sweeteners 0.2 — 0.2^(C)Cinnamon-Menthol Flavor ^(D)Fruity-mint Menthol Flavor *Coolingagent used in the examples may contain ML, MS, MGK, AC, PMC, TCA orcombinations

Breath Freshening Examples

To evaluate chewing gum formulations made with a cinnamon flavor and lowlevels of mint flavor, along with physiological cooling agents forbreath freshening, the following samples were made:

TABLE 53 Example 263 (comparative) Example 264 Example 265 Example 266Gum Base 19.46% 19.46% 19.46% 19.46% Cinnamon 1.29% 1.29% 1.29% 1.39%Flavor Peppermint 0.10% 0.10% 0.10% — Flavor WS-3 — 0.10% 0.10% 0.10%Menthone — — 0.20% — Glycerol Ketal Sugar 62.24% 62.14% 61.94% 62.14%Corn Syrup 15.57% 15.57% 15.57% 15.57% Glycerin 0.67% 0.67% 0.67% 0.67%Color 0.67% 0.67% 0.67% 0.67% TOTAL 100.00 100.00 100.00 100.00

Informal evaluation showed Examples 263, 264 and 265 samples to have aclean cinnamon flavor with only a slight mint note. However, Examples264, 265 and 266 had noticeably higher cooling.

A trained panel of eight chewers were given a cracker smeared withgarlic/onion cream cheese. They then chewed the gums of Examples 263(comparative) and 264 (inventive) and rated “Fresh Breath”, “Odor” and“Effectiveness for Breath Freshening” at 0.5, 1, 2, 3, 4, 5, 6, 7, 9,11, 13 and 15 minutes. The gum was discarded and additional ratings weremade at 5 and 10 minutes afterward (P5, P10). As can be seen from thegraphs of FIGS. 1-3, which show the test results, the inventivecomposition had significantly better scores for each of the three ratedproperties in FIG. 1 it can be seen that the inventive gum (Example 264)produced generally higher scores for breath freshness. FIG. 2 rates theodor of the breath, and the Example 264 inventive gum produced lowerodor ratings than the comparative gum (Example 263). FIG. 3 shows thatthe effectiveness for breath freshening was considered generally higherfor the inventive gum (Example 264) than for the comparative gum(Example 263).

The following formulas are also illustrative of the invention.

TABLE 54 Example 267 Example 268 Example 269 Gum Base 24.00% 24.00%24.00% Sorbitol 55.10% 55.00% 55.00% Mannitol 7.00% 7.00% 7.00%Hydrogenated Starch 6.50% 6.50% 6.50% Hydrolysate Syrup Glycerin 5.00%5.00% 5.00% Cinnamon Flavor 1.30% 1.30% 1.30% WS-3 — 0.10% 0.20%Menthone Glycerol Ketal 0.20% 0.20% 0.10% Red Color 0.50% 0.50% 0.50%Aspartame 0.15% 0.15% 0.15% Encapsulated Aspartame 0.25% 0.25% 0.25%TOTAL 100.00 100.00 100.00

The samples will have a clean cinnamon flavor and enhanced breathfreshening.

TABLE 55 Example 270 Example 271 Example 272 Gum Base 24.00% 24.00%24.00% Sorbitol 55.00% 55.00% 54.90% Mannitol 7.00% 7.00% 7.00%Hydrogenated Starch 6.50% 6.50% 6.50% Hydrolysate Syrup Glycerin 5.00%5.00% 5.00% Cinnamon Flavor 1.30% 1.30% 1.30% WS-23 — 0.10% 0.20%Menthyl Lactate 0.20% 0.20% 0.10% Red Color 0.50% 0.50% 0.50% Aspartame0.15% 0.15% 0.15% Encapsulated Aspartame 0.25% 0.25% 0.25% MenthylSuccinate 0.10% — 0.10% TOTAL 100.00 100.00 100.00

The samples will have a clean cinnamon flavor and enhanced breathfreshening.

It should be appreciated that the methods and compositions of thepresent invention are capable of being incorporated in the form of avariety of embodiments, only a few of which have been illustrated anddescribed above. The invention may be embodied in other forms withoutdeparting from its spirit or essential characteristics. It will beappreciated that the addition of some other ingredients, process steps,materials or components not specifically included will have an adverseimpact on the present invention. The best mode of the invention maytherefore exclude ingredients, process steps, materials or componentsother than those listed above for inclusion or use in the invention.However, the described embodiments are to be considered in all respectsonly as illustrative and not restrictive, and the scope of the inventionis, therefore, indicated by the appended claims rather than by theforegoing description. All changes which come within the meaning andrange of equivalency of the claims are to be embraced within theirscope.

1. A method of producing chewing gum with physiological cooling agentscomprising the steps of: a) mixing at least two physiological coolingagents together with a release modification material; b) treating thecooling agents to provide a modified release; and c) adding a quantityof the modified release cooling agents to a chewing gum composition toprovide a cooling agent level in the gum of from about 0.001% to about2%.
 2. The method of claim 1 wherein the physiological cooling agentsare selected from the group consisting of N-substituted p-menthanecarboxamides, menthyl lactate, menthone glycerol ketal, 3−/−menthoxypropane-1,2-diol, menthyl succinate and combinations thereof. 3.The method of claim 1 wherein the cooling agents are treated by anencapsulation process.
 4. The method of claim 3 wherein the coolingagents are encapsulated by a spray drying process.
 5. The method ofclaim 3 wherein the cooling agents are encapsulated by a fluid bedcoating process.
 6. The method of claim 1 wherein the cooling agents aretreated by being entrapped in an extrusion process.
 7. A chewing gummade according to the method of claim
 1. 8. A chewing gum compositioncomprising: a) about 5% to about 95% gum base; b) about 5% to about 95%bulking and sweetening agent; and c) about 0.1 to about 10% flavoringagent wherein the flavoring agent comprises an acyclic carboxamide andone or more other physiological cooling agents.
 9. The chewing gumcomposition of claim 8 wherein the acyclic carboxamide comprisesN-2,3-trimethyl-2-isopropyl butanamide.
 10. The chewing gum compositionof claim 9 wherein the one or more other physiological cooling agentscomprises menthyl succinate.
 11. A chewing gum composition comprising:a) about 5% to about 95% gum base; b) about 5% to about 95% bulking andsweetening agent; and c) about 0.1 to about 10% flavoring agent whereinthe flavoring agent comprises an acyclic carboxamide and menthol. 12.The chewing gum composition of claim 11 wherein the acyclic carboxamidecomprises N-2,3-trimethyl-2-isopropyl butanamide.
 13. The chewing gumcomposition of claim 12 wherein the flavoring agent further comprisesmenthyl succinate.
 14. A method of producing a chewing gum with aphysiological cooling agent comprising the steps of: a) mixing aphysiological cooling agent comprising an acyclic carboxamide togetherwith a release modification material; b) treating the cooling agent toprovide a modified release; and c) adding a quantity of the modifiedrelease cooling agent to a chewing gum composition to provide a coolingagent level in the gum of from about 0.001% to about 1%.
 15. The methodof claim 14 wherein the acyclic carboxamide comprisesN-2,3-trimethyl-2-isopropyl butanamide.